Crystal structure of [(2R,3R,4S)-3,4-bis(acet­yloxy)-5-iodo-3,4-di­hydro-2H-pyran-2-yl]methyl acetate

Zukerman-Schpector, J.; Caracelli, I.; Stefani, H.A.; Shamim, A.; Tiekink, E.R.T.

doi:10.1107/S205698901402564X

organic compounds

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ISSN: 2056-9890

Volume 71| Part 1| January 2015| Pages o53-o54

https://doi.org/10.1107/S205698901402564X

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Crystal structure of [(2R,3R,4S)-3,4-bis(acetyloxy)-5-iodo-3,4-dihydro-2H-pyran-2-yl]methyl acetate

Julio Zukerman-Schpector,^a ^* Ignez Caracelli,^b Hélio A. Stefani,^c Anwar Shamim ^d and Edward R.T. Tiekink ^e

^aDepartmento de Química, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil, ^bDepartmento de Física, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil, ^cDepartamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo-SP, Brazil, ^dInstituto de Química, Universidade de São Paulo, São Paulo-SP, Brazil, and ^eDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: julio@power.ufscar.br

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 21 November 2014; accepted 24 November 2014; online 1 January 2015)

In the title compound, C₁₂H₁₅IO₇, the 3,4-dihydro-2H-pyran ring is in a distorted half-boat conformation with the atom bearing the acetyloxy group adjacent to the C atom bearing the methylacetate group lying 0.633 (6) Å above the plane of the remaining ring atoms (r.m.s. deviation = 0.0907 Å). In the crystal, molecules are linked into a supramolecular chain along the a axis through two C—H⋯O interactions to the same acceptor carbonyl O atom; these chains pack with no specific intermolecular interactions between them.

Keywords: Crystal structure; carbohydrate; conformation; C—H⋯O interactions; crystal structure.

CCDC reference: 1035669

1. Related literature

For the structure of the unsubstituted parent compound, determined three times, and having a distorted half-boat conformation, see: Vangehr et al. (1979 ); Krajewski et al. (1979 ); Voelter et al. (1981 ).

2. Experimental

2.1. Crystal data

C₁₂H₁₅IO₇
M_r = 398.14
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.9048 (2) Å
b = 8.7521 (2) Å
c = 22.7094 (5) Å
V = 1571.12 (6) Å³
Z = 4
Mo Kα radiation
μ = 2.06 mm⁻¹
T = 293 K
0.35 × 0.24 × 0.11 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.601, T_max = 0.745
6116 measured reflections
2818 independent reflections
2456 reflections with I > 2σ(I)
R_int = 0.019

2.3. Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.071
S = 1.04
2818 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.58 e Å⁻³
Absolute structure: Flack x determined using 925 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter: 0.000 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O6ⁱ	0.93	2.58	3.448 (7)	156
C3—H3⋯O6ⁱⁱ	0.98	2.55	3.383 (6)	143
Symmetry codes: (i) x-1, y, z; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SIR (Burla et al., 2014 ; program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1035669

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S205698901402564X/hb7323sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698901402564X/hb7323Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S205698901402564X/hb7323Isup3.cml

checkCIF report

Experimental top

Synthesis and crystallization top

To a solution of 3,4,6-tri-oxoacetyl-D-Glucal (3 mmol) in acetonitrile (9 mL) at 373 K under a N₂ atmosphere was added N-iodosuccinimide (3.6 mmol) and silver nitrate (0.6 mmol) as catalyst followed by stirring for 4 h. After consumption of the starting material (TLC monitoring), the reaction mixture was filtered through a sintered funnel (using Celite) and the filtrate was then evaporated giving a crude product which was purified by silica gel column chromatography (20-30% of EtOAc/hexane) to obtain the title compound. Suitable crystals were obtained by keeping the EtOAc solution of the product at 277 K for 48 h.

¹H NMR (CDCl₃, 300 MHz): δ 6.73 (s, 1H), 5.44 (d, J = 5.1 Hz, 1H), 5.18 (dd, J = 5.1, 7.0 Hz, 1>H), 4.37-4.30 (m, 2H), 4.08-4.18 (m, 1H), 2.09 (s, 3H), 2.05 (s, 3H), 2.04 (s, 3H). ¹³C NMR (CDCl₃, 75 MHz) δ = 170.5, 170.3, 169.4, 149.4, 74.0, 70.6, 67.6, 66.3, 61.0, 20.9, 20.8, 20.7 ppm. HRMS: calcd. for C₁₂H₁₅IO₇ [M + H]⁺ 397.9862; found: 397.9863.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H = 0.93 to 0.98 Å) and were included in the refinement in the riding model approximation, with U_iso(H) = 1.2–1.5U_eq(C).

Results and discussion top

The 3,4-dihydro-2H-pyran ring in the title compound, Fig. 1, is in a distorted half-boat conformation as reflected in the conformational parameters: the puckering amplitude (Q) = 0.497 (5) Å, θ = 52.6 (6)° and φ = 268.6 (7)°. In this conformation, the C4 atom lies 0.633 (6) Å above the plane of the remaining ring atoms which have a r.m.s. of 0.0907 Å. The substituents at the C3 and C4 sites occupy equatorial positions while that at atom C5 is bisectional. The crystal structure of the unsubstituted parent compound has been reported three times and also adopts a distorted half-boat conformation (Vangehr et al., 1979; Krajewski et al., 1979; Voelter et al., 1981).

In the crystal , the molecules are linked via two independent C—H···O interactions, Table 1, involving the same carbonyl-O6 atom as acceptor. The resulting supramolecular architecture is a chain parallel to the a axis, Fig. 2. These chains pack with no specific intermolecular interactions between them, Fig. 3.

Related literature top

For the structure of the unsubstituted parent compound, determined three times, and having a distorted half-boat conformation, see: Vangehr et al. (1979); Krajewski et al. (1979); Voelter et al. (1981).

Structure description top

For the structure of the unsubstituted parent compound, determined three times, and having a distorted half-boat conformation, see: Vangehr et al. (1979); Krajewski et al. (1979); Voelter et al. (1981).

Synthesis and crystallization top

Refinement details top

Carbon-bound H-atoms were placed in calculated positions (C—H = 0.93 to 0.98 Å) and were included in the refinement in the riding model approximation, with U_iso(H) = 1.2–1.5U_eq(C).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SIR (Burla et al., 2014; program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound showing displacement ellipsoids at the 35% probability level.
	Fig. 2. A view of the supramolecular chain along the a axis mediated by C—H···O interactions (orange dashed lines).
	Fig. 3. A view in projection down the a axis of the unit-cell contents. The C—H···O interactions are shown as orange dashed lines.

[(2R,3R,4S)-3,4-Bis(acetyloxy)-5-iodo-3,4-dihydro-2H-pyran-2-yl]methyl acetate top

Crystal data top

C₁₂H₁₅IO₇	D_x = 1.683 Mg m⁻³
M_r = 398.14	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 3256 reflections
a = 7.9048 (2) Å	θ = 2.7–25.1°
b = 8.7521 (2) Å	µ = 2.06 mm⁻¹
c = 22.7094 (5) Å	T = 293 K
V = 1571.12 (6) Å³	Irregular, colourless
Z = 4	0.35 × 0.24 × 0.11 mm
F(000) = 784

Data collection top

Bruker APEXII CCD diffractometer	2456 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.019
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	θ_max = 25.4°, θ_min = 1.8°
T_min = 0.601, T_max = 0.745	h = −9→5
6116 measured reflections	k = −7→10
2818 independent reflections	l = −27→27

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.028	H-atom parameters constrained
wR(F²) = 0.071	w = 1/[σ²(F_o²) + (0.0299P)² + 0.3563P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2818 reflections	Δρ_max = 0.28 e Å⁻³
184 parameters	Δρ_min = −0.58 e Å⁻³
0 restraints	Absolute structure: Flack x determined using 925 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.000 (11)

Crystal data top

C₁₂H₁₅IO₇	V = 1571.12 (6) Å³
M_r = 398.14	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.9048 (2) Å	µ = 2.06 mm⁻¹
b = 8.7521 (2) Å	T = 293 K
c = 22.7094 (5) Å	0.35 × 0.24 × 0.11 mm

Data collection top

Bruker APEXII CCD diffractometer	2818 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2456 reflections with I > 2σ(I)
T_min = 0.601, T_max = 0.745	R_int = 0.019
6116 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	H-atom parameters constrained
wR(F²) = 0.071	Δρ_max = 0.28 e Å⁻³
S = 1.04	Δρ_min = −0.58 e Å⁻³
2818 reflections	Absolute structure: Flack x determined using 925 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
184 parameters	Absolute structure parameter: 0.000 (11)
0 restraints

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I	0.55529 (6)	0.37319 (5)	0.49032 (2)	0.1044 (2)
O1	0.5090 (4)	0.9803 (5)	0.31664 (17)	0.0798 (10)
O2	0.7080 (7)	1.1290 (7)	0.2782 (3)	0.141 (2)
O3	0.8630 (3)	0.8456 (4)	0.37365 (13)	0.0609 (8)
O4	0.8637 (5)	0.7615 (5)	0.28034 (15)	0.0839 (11)
O5	0.8078 (4)	0.5163 (4)	0.38956 (12)	0.0603 (8)
O6	1.0344 (5)	0.4998 (6)	0.44747 (19)	0.1042 (14)
O7	0.4218 (4)	0.8098 (5)	0.41934 (15)	0.0749 (9)
C1	0.5672 (6)	0.5851 (6)	0.44833 (17)	0.0637 (11)
C2	0.4291 (6)	0.6670 (7)	0.44323 (19)	0.0728 (14)
H2	0.3287	0.6246	0.4569	0.087*
C3	0.5830 (5)	0.8834 (6)	0.41154 (19)	0.0653 (12)
H3	0.6264	0.9136	0.4502	0.078*
C4	0.7049 (5)	0.7701 (5)	0.38426 (17)	0.0514 (10)
H4	0.6585	0.7334	0.3468	0.062*
C5	0.7335 (5)	0.6361 (6)	0.42476 (16)	0.0576 (10)
H5	0.8095	0.6647	0.4570	0.069*
C6	0.5543 (7)	1.0241 (6)	0.3756 (3)	0.0825 (14)
H6A	0.4643	1.0846	0.3929	0.099*
H6B	0.6564	1.0855	0.3749	0.099*
C7	0.5931 (7)	1.0403 (7)	0.2711 (3)	0.0887 (18)
C8	0.5349 (9)	0.9756 (11)	0.2140 (3)	0.121 (3)
H8A	0.5497	0.8667	0.2143	0.181*
H8B	0.6000	1.0190	0.1824	0.181*
H8C	0.4174	0.9993	0.2083	0.181*
C9	0.9308 (6)	0.8302 (5)	0.3190 (2)	0.0607 (11)
C10	1.0949 (6)	0.9124 (7)	0.3156 (3)	0.0869 (16)
H10A	1.0799	1.0066	0.2946	0.130*
H10B	1.1762	0.8500	0.2954	0.130*
H10C	1.1348	0.9338	0.3547	0.130*
C11	0.9611 (6)	0.4617 (6)	0.4043 (2)	0.0653 (11)
C12	1.0198 (7)	0.3483 (8)	0.3605 (3)	0.0952 (19)
H12A	1.1130	0.2915	0.3766	0.143*
H12B	1.0556	0.4002	0.3254	0.143*
H12C	0.9290	0.2796	0.3512	0.143*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I	0.1334 (4)	0.0973 (3)	0.0825 (3)	−0.0195 (3)	0.0270 (2)	0.0107 (2)
O1	0.0605 (18)	0.092 (3)	0.087 (2)	−0.0091 (16)	−0.0051 (16)	0.015 (2)
O2	0.126 (4)	0.127 (4)	0.169 (5)	−0.048 (4)	0.012 (3)	0.045 (4)
O3	0.0480 (14)	0.074 (2)	0.0606 (16)	−0.0122 (14)	0.0004 (12)	−0.0116 (16)
O4	0.080 (2)	0.114 (3)	0.058 (2)	−0.022 (2)	0.0163 (18)	−0.013 (2)
O5	0.0586 (16)	0.076 (2)	0.0461 (15)	0.0052 (15)	−0.0067 (13)	−0.0102 (15)
O6	0.075 (2)	0.146 (4)	0.092 (3)	0.021 (3)	−0.030 (2)	−0.026 (3)
O7	0.0491 (16)	0.105 (3)	0.0702 (19)	0.0004 (17)	0.0113 (15)	−0.0053 (19)
C1	0.069 (3)	0.081 (3)	0.0416 (19)	−0.010 (3)	0.0058 (19)	−0.006 (2)
C2	0.066 (3)	0.102 (4)	0.050 (2)	−0.018 (3)	0.017 (2)	−0.014 (3)
C3	0.056 (2)	0.085 (3)	0.055 (2)	−0.006 (3)	0.0020 (18)	−0.020 (3)
C4	0.0427 (19)	0.069 (3)	0.042 (2)	−0.0070 (19)	−0.0024 (17)	−0.011 (2)
C5	0.059 (2)	0.077 (3)	0.0368 (18)	−0.011 (2)	−0.0018 (16)	−0.011 (2)
C6	0.068 (3)	0.073 (3)	0.107 (4)	0.001 (3)	0.008 (3)	−0.011 (3)
C7	0.063 (3)	0.086 (4)	0.118 (5)	0.007 (3)	0.004 (3)	0.041 (4)
C8	0.102 (4)	0.174 (8)	0.086 (4)	0.001 (5)	−0.008 (4)	0.057 (5)
C9	0.052 (2)	0.065 (3)	0.065 (3)	0.002 (2)	0.010 (2)	0.002 (2)
C10	0.059 (3)	0.092 (4)	0.109 (4)	−0.010 (3)	0.017 (3)	0.007 (3)
C11	0.058 (2)	0.084 (3)	0.055 (2)	0.001 (3)	0.003 (2)	0.005 (2)
C12	0.086 (4)	0.116 (5)	0.084 (4)	0.023 (4)	0.010 (3)	−0.013 (4)

Geometric parameters (Å, º) top

I—C1	2.087 (5)	C4—C5	1.507 (6)
O1—C7	1.336 (7)	C4—H4	0.9800
O1—C6	1.438 (7)	C5—H5	0.9800
O2—C7	1.205 (8)	C6—H6A	0.9700
O3—C9	1.359 (5)	C6—H6B	0.9700
O3—C4	1.434 (5)	C7—C8	1.490 (10)
O4—C9	1.188 (6)	C8—H8A	0.9600
O5—C11	1.345 (6)	C8—H8B	0.9600
O5—C5	1.444 (5)	C8—H8C	0.9600
O6—C11	1.186 (6)	C9—C10	1.486 (7)
O7—C2	1.364 (7)	C10—H10A	0.9600
O7—C3	1.439 (5)	C10—H10B	0.9600
C1—C2	1.311 (7)	C10—H10C	0.9600
C1—C5	1.488 (6)	C11—C12	1.479 (7)
C2—H2	0.9300	C12—H12A	0.9600
C3—C6	1.495 (8)	C12—H12B	0.9600
C3—C4	1.515 (6)	C12—H12C	0.9600
C3—H3	0.9800

C7—O1—C6	119.4 (5)	O1—C6—H6B	109.9
C9—O3—C4	116.8 (3)	C3—C6—H6B	109.9
C11—O5—C5	119.1 (3)	H6A—C6—H6B	108.3
C2—O7—C3	114.9 (4)	O2—C7—O1	121.7 (7)
C2—C1—C5	122.6 (5)	O2—C7—C8	126.4 (6)
C2—C1—I	119.3 (4)	O1—C7—C8	111.8 (5)
C5—C1—I	118.1 (4)	C7—C8—H8A	109.5
C1—C2—O7	124.9 (4)	C7—C8—H8B	109.5
C1—C2—H2	117.6	H8A—C8—H8B	109.5
O7—C2—H2	117.6	C7—C8—H8C	109.5
O7—C3—C6	107.6 (4)	H8A—C8—H8C	109.5
O7—C3—C4	108.7 (4)	H8B—C8—H8C	109.5
C6—C3—C4	114.3 (4)	O4—C9—O3	123.3 (4)
O7—C3—H3	108.7	O4—C9—C10	126.6 (4)
C6—C3—H3	108.7	O3—C9—C10	110.1 (4)
C4—C3—H3	108.7	C9—C10—H10A	109.5
O3—C4—C5	109.3 (3)	C9—C10—H10B	109.5
O3—C4—C3	108.7 (3)	H10A—C10—H10B	109.5
C5—C4—C3	110.8 (4)	C9—C10—H10C	109.5
O3—C4—H4	109.3	H10A—C10—H10C	109.5
C5—C4—H4	109.3	H10B—C10—H10C	109.5
C3—C4—H4	109.3	O6—C11—O5	123.1 (5)
O5—C5—C1	109.9 (4)	O6—C11—C12	126.2 (5)
O5—C5—C4	106.8 (3)	O5—C11—C12	110.7 (4)
C1—C5—C4	108.7 (4)	C11—C12—H12A	109.5
O5—C5—H5	110.5	C11—C12—H12B	109.5
C1—C5—H5	110.5	H12A—C12—H12B	109.5
C4—C5—H5	110.5	C11—C12—H12C	109.5
O1—C6—C3	109.1 (4)	H12A—C12—H12C	109.5
O1—C6—H6A	109.9	H12B—C12—H12C	109.5
C3—C6—H6A	109.9

C5—C1—C2—O7	−3.9 (7)	C2—C1—C5—C4	−13.0 (6)
I—C1—C2—O7	176.7 (3)	I—C1—C5—C4	166.4 (3)
C3—O7—C2—C1	−13.7 (6)	O3—C4—C5—O5	−76.7 (4)
C2—O7—C3—C6	170.0 (4)	C3—C4—C5—O5	163.5 (3)
C2—O7—C3—C4	45.7 (5)	O3—C4—C5—C1	164.8 (3)
C9—O3—C4—C5	108.8 (4)	C3—C4—C5—C1	45.0 (4)
C9—O3—C4—C3	−130.1 (4)	C7—O1—C6—C3	−128.3 (5)
O7—C3—C4—O3	177.0 (3)	O7—C3—C6—O1	−68.9 (5)
C6—C3—C4—O3	56.8 (5)	C4—C3—C6—O1	51.9 (5)
O7—C3—C4—C5	−62.8 (4)	C6—O1—C7—O2	1.0 (8)
C6—C3—C4—C5	177.0 (4)	C6—O1—C7—C8	177.0 (5)
C11—O5—C5—C1	−121.9 (4)	C4—O3—C9—O4	1.9 (6)
C11—O5—C5—C4	120.4 (4)	C4—O3—C9—C10	−179.0 (4)
C2—C1—C5—O5	−129.5 (5)	C5—O5—C11—O6	5.3 (7)
I—C1—C5—O5	49.9 (4)	C5—O5—C11—C12	−175.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O6ⁱ	0.93	2.58	3.448 (7)	156
C3—H3···O6ⁱⁱ	0.98	2.55	3.383 (6)	143

Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+3/2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O6ⁱ	0.93	2.58	3.448 (7)	156
C3—H3···O6ⁱⁱ	0.98	2.55	3.383 (6)	143

Symmetry codes: (i) x−1, y, z; (ii) x−1/2, −y+3/2, −z+1.

Acknowledgements

We thank Professor Regina H. A. Santos from IQSC–USP for the X-ray data collection. The Brazilian agencies CNPq (305626/2013–2 to JZS; 306121/2013-2 to IC; 308320/2010-7 to HAS) and FAPESP are acknowledged for financial support.

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Volume 71| Part 1| January 2015| Pages o53-o54

https://doi.org/10.1107/S205698901402564X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of [(2R,3R,4S)-3,4-bis­(acet­yl­oxy)-5-iodo-3,4-di­hydro-2H-pyran-2-yl]methyl acetate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of [(2R,3R,4S)-3,4-bis(acetyloxy)-5-iodo-3,4-dihydro-2H-pyran-2-yl]methyl acetate