Synthesis of (1 S ,2 S ,3 R ,4 R ,5 S )-methyl-3,5-di- O -benzyl-2- O -benzoyl-α-L-talofuranoside

M. J. Khalikova; Халикова М. Дж.; U. A. Roziqov; Розиков У. А.; A. S. Skrylkova; Скрылькова А. С.; D. M. Egorov; Егоров Дмитрий Михайлович; S. Sh. Safarov; Сафаров Сайфидин Шахобидинович

doi:10.31857/S0514749224040137

Synthesis of (1S,2S,3R,4R,5S)-methyl-3,5-di-O-benzyl-2-O-benzoyl-α-L-talofuranoside

Authors: Khalikova M.J.¹, Roziqov U.A.¹, Skrylkova A.S.², Egorov D.M.², Safarov S.S.¹
Affiliations:
1. V. I. Nikitin Institute of Chemistry, National Academy of Sciences of Tajikistan
2. St. Petersburg State Institute of Technology (Technical University)
Issue: Vol 60, No 4 (2024)
Pages: 516-522
Section: Articles
URL: https://ruspoj.com/0514-7492/article/view/672180
DOI: https://doi.org/10.31857/S0514749224040137
EDN: https://elibrary.ru/RYNANK
ID: 672180

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Abstract

The article presents a method for the preparation of (1S,2S,3R,4R,5S)-methyl-3,5-di-O-benzyl-2-O-benzoyl-α-L-talofuranoside from (1S,2S,3R,4R,5S)-methyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-L-talofuranoside by successive treatment of the latter with a 20% solution of hydrochloric acid in aqueous methanol, followed by treatment with benzoyl chloride in dry pyridine. A promising use of methyl (1S,2S,3R,4R,5S)-3,5-di-O-benzyl-2-O-benzoyl-α-L-talofuranoside for the synthesis of new modified nucleosides after its acetylation has also been shown.

Keywords

(1S,2S,3R,4R,5S)-methyl-3,5-di-O-benzyl-2-O-benzoyl-α-L-talofuranoside, (1S,2S,3R,4R,5S)-methyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-L-talofuranoside, way for the synthesis of new modified nucleosides

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