Synthesis of 2,3-unsaturated thioglycopyranosides mediated by lithium tetrafluoroborate

被引：24

作者：

Babu, BS ^{[1
]}

Balasubramanian, KK ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Madras 600036, Tamil Nadu, India

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 31期

关键词：

Ferrier rearrangement; thioglycosides; glycosides; lithium fluoroborate; Lewis acid;

D O I：

10.1016/S0040-4039(99)01111-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of tri-O acetyl-D-glucal 1 with diverse thiols 2-7 in the presence of LiBF4 in CH3CN, furnished aryl/alkyl 2,3-unsaturated thioglycopyranosides 8-13 (56-72%). (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：5777 / 5778

页数：2

共 11 条

[1] AMATORE C, 1994, J APPL ELECTROCHEM, V24, P715
[2] REGIOSELECTIVE SYNTHESIS OF SUBSTITUTED 1-THIOHEX-2-ENOPYRANOSIDES
DUNKERTON, LV
ADAIR, NK
EUSKE, JM
BRADY, KT
ROBINSON, PD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (04) : 845 - 850
[3] UNSATURATED CARBOHYDRATES .9. SYNTHESIS OF 2,3-DIDEOXY-ALPHA-D-ERYTHRO-HEX-2-ENOPYRANOSIDES FROM TRI-O-ACETYL-D-GLUCAL
FERRIER, RJ
PRASAD, N
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (04): : 570 - &
[4] THIOGLYCOSIDES AS GLYCOSYLATING AGENTS IN OLIGOSACCHARIDE SYNTHESIS
FUGEDI, P
GAREGG, PJ
LONN, H
NORBERG, T
[J]. GLYCOCONJUGATE JOURNAL, 1987, 4 (02) : 97 - 108
[5] SYNTHESIS OF THE CORE TRISACCHARIDE OF ESPERAMICIN - CORROBORATION OF THE PROPOSED STRUCTURE FOR ITS REARRANGEMENT PRODUCT AND STABILIZATION OF THE CORE TRISACCHARIDE DOMAIN
HALCOMB, RL
WITTMAN, MD
OLSON, SH
DANISHEFSKY, SJ
GOLIK, J
WONG, H
VYAS, D
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (13) : 5080 - 5082
[6] CHEMISTRY OF BETA-TRIMETHYLSILYLETHANOL .2. A NEW METHOD FOR PROTECTION OF AN ANOMERIC CENTER IN PYRANOSIDES
LIPSHUTZ, BH
PEGRAM, JJ
MOREY, MC
[J]. TETRAHEDRON LETTERS, 1981, 22 (46) : 4603 - 4606
[7] HYDROLYSIS OF ACETALS AND KETALS USING LIBF4
LIPSHUTZ, BH
HARVEY, DF
[J]. SYNTHETIC COMMUNICATIONS, 1982, 12 (04) : 267 - 277
[8] CLEAVAGE OF TERT-BUTYLDIMETHYLSILYL ETHERS BY TETRAFLUOROBORATE SALTS
METCALF, BW
BURKHART, JP
JUND, K
[J]. TETRAHEDRON LETTERS, 1980, 21 (01) : 35 - 36
[9] ACID-CATALYZED REACTION OF THIOLS WITH ALKYL 2,3-DIDEOXY-GLYC-2-ENOPYRANOSIDES OR GLYCALS
PRIEBE, W
ZAMOJSKI, A
[J]. TETRAHEDRON, 1980, 36 (02) : 287 - 297
[10] RECENT ADVANCES IN GLYCOSYLATION REACTIONS
SINAY, P
[J]. PURE AND APPLIED CHEMISTRY, 1991, 63 (04) : 519 - 528

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