Diastereoselective synthesis of C-glycosylphosphonates via free-radical glycosylation

被引：36

作者：

Junker, HD ^{[1
]}

Fessner, WD ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Dept Organ Chem, D-52056 Aachen, Germany

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 3-4期

关键词：

D O I：

10.1016/S0040-4039(97)10498-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A single step approach for the diastereoselective synthesis of C-glycosidic sugar phosphonates was developed by utilizing a free radical coupling to dialkyl vinylphosphonates to give the title compounds in moderate yield. The method is broadly applicable to sugars, deoxysugars, aminosugars, and oligosaccharides. (C) 1997 Elsevier Science Ltd. All rights reserved.

引用

页码：269 / 272

页数：4

共 17 条

[1]

ARTH HL, IN PRESS CARBOHYDR R

[2] NEW SYNTHESIS OF SUGAR, NUCLEOSIDE AND ALPHA-AMINO-ACID PHOSPHONATES [J].

BARTON, DHR ;

GERO, SD ;

QUICLETSIRE, B ;

SAMADI, M .

TETRAHEDRON, 1992, 48 (09) :1627-1636

[3] DEOXY-NITROSUGARS .6. STEREOELECTRONIC CONTROL IN THE REDUCTIVE DENITRATION OF TERTIARY NITRO ETHERS - A SYNTHESIS OF C-GLYCOSIDES [J].

BAUMBERGER, F ;

VASELLA, A .

HELVETICA CHIMICA ACTA, 1983, 66 (07) :2210-2222

[4] Stereoselective synthesis of the isosteric phosphono analogues of N-acetyl-alpha-D-glucosamine 1-phosphate and N-acetyl-alpha-D-mannosamine 1-phosphate [J].

Casero, F ;

Cipolla, L ;

Lay, L ;

Nicotra, F ;

Panza, L ;

Russo, G .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3428-3432

[5] ORGANOSILANES AS RADICAL-BASED REDUCING AGENTS IN SYNTHESIS [J].

CHATGILIALOGLU, C .

ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (04) :188-194

[6] CONFORMATION OF GLYCOSYL RADICALS - RADICAL STABILIZATION BY BETA-CO BONDS [J].

DUPUIS, J ;

GIESE, B ;

RUEGGE, D ;

FISCHER, H ;

KORTH, HG ;

SUSTMANN, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (11) :896-898

[7] PHOSPHONATES AS ANALOGS OF NATURAL PHOSPHATES [J].

ENGEL, R .

CHEMICAL REVIEWS, 1977, 77 (03) :349-367

[8]

Engel R., 1992, HDB ORGANOPHOSPHORUS, P559

[9] ANOMERIC EFFECT OF RADICALS [J].

GIESE, B ;

DUPUIS, J .

TETRAHEDRON LETTERS, 1984, 25 (13) :1349-1352

[10] THE STEREOSELECTIVITY OF INTERMOLECULAR FREE-RADICAL REACTIONS [J].

GIESE, B .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1989, 28 (08) :969-980

← 1 2 →