STEREOSPECIFIC 1,2-ETHYL(PHENYL)THIO GROUP MIGRATION IN SUGARS - STEREOCONTROLLED SYNTHESIS OF PRECURSORS TO ALPHA-2-DEOXYGLYCOSIDES AND BETA-2-DEOXYGLYCOSIDES

被引：26

作者：

ZUURMOND, HM

VANDERKLEIN, PAM

VANDERMAREL, GA

VANBOOM, JH

机构：

[1] Gorlaeus Laboratories, 2300 RA Leiden

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 15期

关键词：

D O I：

10.1016/0040-4039(92)88142-R

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Iodonium ion (NIS/TfOH, cat.) assisted glycosylation of a sugar acceptor with properly protected ethyl(phenyl)-2-O-phenoxythiocarbonyl 1-thio-beta-D-gluco- or 1-thio-alpha-D-mannopyranoside donors gives the respective 1,2-trans linked 2'-ethyl(phenyl)thio-2'-deoxy-alpha-D-manno- or beta-D-glucopyranosides.

引用

页码：2063 / 2066

页数：4

共 17 条

[1] A STEREOSPECIFIC APPROACH TOWARDS THE SYNTHESIS OF 2-DEOXY ALPHA-GLYCOSIDE AND BETA-GLYCOSIDE BASED ON A 1,2-ETHYL (PHENYL) THIO GROUP MIGRATION
ZUURMOND, HM
VANDERKLEIN, PAM
VANDERMAREL, GA
VANBOOM, JH
TETRAHEDRON, 1993, 49 (29) : 6501 - 6514
[2] INCIDENCE AND AVOIDANCE OF STEREOSPECIFIC 1,2-ETHYLTHIO GROUP MIGRATION DURING THE SYNTHESIS OF ETHYL 1-THIO-ALPHA-L-RHAMNOPYRANOSIDE 2,3-ORTHOESTER
AUZANNEAU, FI
BUNDLE, DR
CARBOHYDRATE RESEARCH, 1991, 212 : 13 - 24
[3] STEREOSPECIFIC 1,2-MIGRATIONS IN CARBOHYDRATES - STEREOCONTROLLED SYNTHESIS OF ALPHA-2-DEOXYGLYCOSIDE BETA-2-DEOXYGLYCOSIDE
NICOLAOU, KC
LADDUWAHETTY, T
RANDALL, JL
CHUCHOLOWSKI, A
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (09) : 2466 - 2467
[4] Stereoselective synthesis of 2-S-ethyl(phenyl)-2-thio-β-glucopyranosides via 1,2-migration and concurrent glycosidation of ethyl(phenyl) 2,3-orthoester-1-thio-α-mannopyranosides
Yang, ZY
Yu, B
CARBOHYDRATE RESEARCH, 2001, 333 (02) : 105 - 114
[5] NOVEL GLYCOSIDATION METHOD USING 2,6-ANHYDRO-2-THIO SUGARS FOR STEREOCONTROLLED SYNTHESIS OF 2,6-DIDEOXY-ALPHA-GLYCOSIDES AND 2,6-DIDEOXY-BETA-GLYCOSIDES
TOSHIMA, K
MUKAIYAMA, S
NOZAKI, Y
INOKUCHI, H
NAKATA, M
TATSUTA, K
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (20) : 9042 - 9051
[6] OXAZOLINE SYNTHESIS OF 1,2-TRANS-2-ACETAMIDO-2-DEOXYGLYCOSIDES - GLYCOSYLATION WITH 2-METHYL-(3,4,6-TRI-ORTHO-ACETYL-1,2-DIDEOXY-ALPHA-D-GALACTOPYRANO)-[2',1' 4,5]-2-OXAZOLINE
JACQUINE.JC
ZURABYAN, SE
KHORLIN, AY
CARBOHYDRATE RESEARCH, 1974, 32 (01) : 137 - 143
[7] 2-DEOXY SUGARS .2. 3-BETA-(2,6-DIDEOXY-ALPHA-D-RIBO-HEXOPYRANOSYL)-14-BETA-HYDROXY-5-BETA-CARD-20(22)-ENOLIDE - A DIRECT METHOD OF SYNTHESIS OF 2-DEOXYGLYCOSIDES INVOLVING A CRYSTALLINE 2-DEOXY-ACYLGLYCOSYL HALIDE
ZORBACH, WW
PAYNE, TA
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (18) : 4979 - 4983
[8] Electrophilic cyclization of 4-thio-but-2-yn-1-ols via 1,2-migration of the thio group: efficient synthesis of 2,4-dihalo-3-thio-substituted furans
Zhou, Hongwei
Yao, Jinzhong
Liu, Guoliang
TETRAHEDRON LETTERS, 2008, 49 (02) : 226 - 228
[9] REARRANGEMENTS OF ORGANOMETALLIC COMPOUNDS .23. CARBON-SKELETAL [1,2] ANIONIC AND RADICAL SIGMATROPIC REARRANGEMENTS - GROUP MIGRATORY APTITUDES AS A PROBE OF CHARGE TYPE IN THE 1,2-SHIFTS OF BETA-PHENYL-BETA-(2-PYRIDYL)ETHYL AND BETA-PHENYL-BETA-(4-PYRIDYL)ETHYL SYSTEMS
EISCH, JJ
KOVACS, CA
CHOBE, P
BOLESLAWSKI, MP
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (20): : 4427 - 4437
[10] 1,2-migration of 2′-oxoalkyl group and concomitant synthesis of 2-C-branched O-,S-glycosides and glycosyl azides via 1,2-cyclopropanated sugars
Shao, HW
Ekthawatchai, S
Chen, CS
Wu, SH
Zou, W
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (12): : 4726 - 4734

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