Chemistry of glycosyl triflates:: Synthesis of β-mannopyranosides (Reprinted from Glycochemistry:: Principles, Synthesis, and Applications, pg 53-75, 2001)

被引：86

作者：

Crich, D ^{[1
]}

机构：

[1] Univ Illinois, Chicago, IL 60612 USA

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 2002年 / 21卷 / 7-9期

关键词：

D O I：

10.1081/CAR-120016486

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

引用

页码：667 / 690

页数：24

共 47 条

[1] A solvation-assisted model for estimating anomeric reactivity. Predicted versus observed trends in hydrolysis of n-pentenyl glycosides [J].

Andrews, CW ;

Rodebaugh, R ;

FraserReid, B .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5280-5289

[2]

BARRESI F, 1996, MODERN METHODS CARBO, P251

[3] INTRAMOLECULAR HYDROGEN-ATOM ABSTRACTION IN CARBOHYDRATES AND NUCLEOSIDES - INVERSION OF AN ALPHA-MANNOPYRANOSIDE TO BETA-MANNOPYRANOSIDE AND GENERATION OF THYMIDINE C-4' RADICALS [J].

BRUNCKOVA, J ;

CRICH, D ;

YAO, QW .

TETRAHEDRON LETTERS, 1994, 35 (36) :6619-6622

[4] Chemistry of 1-alkoxy-1-glycosyl radicals: The manno- and rhamnopyranosyl series. Inversion of alpha- to beta-pyranosides and the fragmentation of anomeric radicals [J].

Crich, D ;

Sun, SX ;

Brunckova, J .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (02) :605-615

[5] Stereoselective sulfoxidation of α-mannopyranosyl thioglycosides:: The exo-anomeric effect in action [J].

Crich, D ;

Mataka, J ;

Sun, SX ;

Lam, KC ;

Rheingold, AL ;

Wink, DJ .

CHEMICAL COMMUNICATIONS, 1998, (24) :2763-2764

[6] Direct synthesis of β-D-xyl-(1→2)-β-D-man-(1→4)-α-D-Glc-OMe:: a trisaccharide component of the Hyriopsis schlegelii glycosphingolipid [J].

Crich, D ;

Dai, ZM .

TETRAHEDRON LETTERS, 1998, 39 (13) :1681-1684

[7] Convergent, stereoselective synthesis of the caloporoside disaccharide [J].

Crich, D ;

Barba, GR .

TETRAHEDRON LETTERS, 1998, 39 (51) :9339-9342

[8] Chemistry of 4,6-O-benzylidene-D-glycopyranosyl triflates:: Contrasting behavior between the gluco and manno series [J].

Crich, D ;

Cai, WL .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13) :4926-4930

[9] Highly diastereoselective α-mannopyranosylation in the absence of participating protecting groups [J].

Crich, D ;

Cai, WL ;

Dai, ZM .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (05) :1291-1297

[10] Are glycosyl triflates intermediates in the sulfoxide glycosylation method? A chemical and H-1, C-13, and F-19 NMR spectroscopic investigation [J].

Crich, D ;

Sun, SX .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (46) :11217-11223

← 1 2 3 4 5 →