New synthesis of alditol thiaheterocycles via ring closure of vicinal bis-cyclic thionocarbonates of alditols

被引：10

作者：

Halila, S ^{[1
]}

Benazza, M ^{[1
]}

Demailly, G ^{[1
]}

机构：

[1] Univ Picardie, Lab Glucides, F-80039 Amiens, France

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 05期

关键词：

alditol; bis-cyclic thionocarbonate; thioheterocycle; thiepane; thiophene; thiopyrane;

D O I：

10.1016/S0040-4039(01)02282-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new thiaheterocyclisation of alditols involving bis-cyclic thionocarbonate derivatives as bielectrophilic intermediates is reported. The polyhydroxylated tetrahydrothiophene, tetrahydropyrane and thiepane rings from erythritol, D,L-threitol, D-arabinitol, D-mannitol and galactitol were efficiently obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：815 / 818

页数：4

相关论文

共 20 条

[1] REGIOCONTROLLED FORMATION OF IODOHYDRINS AND EPOXIDES FROM VIC-DIOLS [J].

ADIYAMAN, M ;

KHANAPURE, SP ;

HWANG, SW ;

ROKACH, J .

TETRAHEDRON LETTERS, 1995, 36 (41) :7367-7370

[2] A new method for the preparation of olefins from vicinal diols [J].

Adiyaman, M ;

Jung, YJ ;

Kim, S ;

Saha, G ;

Powell, WS ;

FitzGerald, GA ;

Rokach, J .

TETRAHEDRON LETTERS, 1999, 40 (21) :4019-4022

[3] REACTION OF DIOL THIOCARBONATES WITH METHYL-IODIDE - SYNTHESIS OF 6-DEOXY-SUGARS [J].

BARTON, DHR ;

STICK, RV .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (18) :1773-1776

[4]

DUREAULT A, 1991, SYNLETT, P225

[5] Synthesis of amphiphilic polyhydroxylated pyrrolidines as potential glycosidase inhibitors [J].

Esposito, A ;

Falorni, M ;

Taddei, M .

TETRAHEDRON LETTERS, 1998, 39 (36) :6543-6546

[6] Heterocyclisation of free or partially protected alditols via their bis-cyclic sulfate derivatives.: Versatile synthesis of aza and thiodeoxyanhydroalditol with erythro, threo, arabino, gulo, talo or manno configuration [J].

Glaçon, V ;

Benazza, M ;

Beaupère, D ;

Demailly, G .

TETRAHEDRON LETTERS, 2000, 41 (26) :5053-5056

[7] Short and efficient synthesis of polyhydroxylated tetrahydrothiophene, tetrahydrothiopyrane and thiepane from bielectrophilic erythro, threo, xylo, ribo, arabino, manno and gluco α,ω-dibromoalditol derivatives [J].

Halila, S ;

Benazza, M ;

Demailly, G .

TETRAHEDRON LETTERS, 2001, 42 (19) :3307-3310

[8] Synthesis of novel, optically active, heterocyclic amino alcohols through desymmetrization of a C2-symmetric cyclic sulfate [J].

Kim, BM ;

Bae, SJ ;

Seomoon, G .

TETRAHEDRON LETTERS, 1998, 39 (38) :6921-6922

[9] VICINAL DIOL CYCLIC THIONOCARBONATES - LIKE CYCLIC SULFATES, AND MORE [J].

KO, SY .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (20) :6250-6251

[10]

Le Merrer Y, 1999, SYNLETT, P1322