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Synthesis of sterols oxygenated in the terminal fragment of their side chains

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Abstract

Methods of stereoselective synthesis of oxysterols are considered by the examples of (25R)-26-hydroxycholesterol, (24S)-24,25-epoxycholesterol, and (24S)-24-hydroxycholesterol containing functional groups in the terminal fragments of their side chain. Special attention is paid to the problems of construction of chiral centers C24 and C25.

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Abbreviations

9-BBN:

9-borabicyclo[3.3.1]-nonane

DHP:

dihydropyran

DMAP:

4-(dimethylamino)pyrydine

HMG-CoA:

hydroxymethyl-glutaryl-coenzime A

LDA:

lithium diisopropylamide

LXR:

Liver X Receptor

MCPBA:

m-chloroperbenzoic acid

MOM:

methoxymethyl

PCC:

pyridinium chlorochromate

PDC:

pyridinium dichromate

PPTS:

pyridinium p-toluenesulfonate

TBS:

tert-butyldimethylsilil

Thp:

tetrahydropyranyl

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Authors and Affiliations

  1. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Kuprevicha 5/2, Minsk, 220141, Belarus

    A. V. Antonchick, V. N. Zhabinskii & V. A. Khripach

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  1. A. V. Antonchick
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  2. V. N. Zhabinskii
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  3. V. A. Khripach
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Correspondence to V. A. Khripach.

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Original Russian Text © A.V. Antonchick, V.N. Zhabinskii, V.A. Khripach, 2008, published in Bioorganicheskaya Khimiya, 2008, Vol. 34, No. 4, pp. 437–450.

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Antonchick, A.V., Zhabinskii, V.N. & Khripach, V.A. Synthesis of sterols oxygenated in the terminal fragment of their side chains. Russ J Bioorg Chem 34, 391–403 (2008). https://doi.org/10.1134/S1068162008040018

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