Preparation of THP-Ester-Derived Pyridinium-Type Salts and their Reactions with Various Nucleophiles

被引：12

作者：

Fujioka, Hiromichi ^{[1
]}

Minamitsuji, Yutaka ^{[1
]}

Moriya, Takahiro ^{[1
]}

Okamoto, Kazuhisa ^{[1
]}

Kubo, Ozora ^{[1
]}

Matsushita, Tomoyo ^{[1
]}

Murai, Kenichi ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2012年 / 7卷 / 08期

关键词：

nucleophilic substitution; protecting groups; salt effect; synthetic methods; tetrahydropyran; ALPHA-SELECTIVE GLYCOSYLATIONS; EFFICIENT DEPROTECTION; BETA-MANNOPYRANOSIDES; COMBINATION; ACETALS; REAGENT; 2,6-DIDEOXYTHIOGLYCOSIDES; CYCLOADDITION; SPECULATION; ALKYLATION;

D O I：

10.1002/asia.201200234

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Nucleophilic substitution at the anomeric positions of tetrahydropyranyl (THP) and related carbohydrate-derived esters that proceeded through pyridinium-type salt intermediates have been developed. Treatment of the 6-substituted a-acetoxy-tetrahydropyrans with TMSOTf (TMS=trimethylsilyl) and 2-substitutited pyridines, such as 2-p-tolylpyridine and 2-methoxypyridine, led to the efficient generation of cis-pyridinium-type salts. These salts reacted with various nucleophiles, such as alcohols, azides, and organozinc reagents, to form nucleophilic-substitution products. A characteristic feature of these processes was that they took place under mild conditions, which did not affect acid-labile protecting groups. Furthermore, the reactions that employed azides and C-nucleophiles generated 2,6-trans products with high degrees of stereoselectivity.

引用

页码：1925 / 1933

页数：9

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