A new method for α-selective glycosylation using a donor, glycosyl methyldiphenylphosphonium iodide, without any assistance of acid promoters

被引：12

作者：

Mukaiyama, T

Kobashi, Y

Shintou, T

机构：

[1] TCI, Kitasato Inst, Ctr Basic Res, Kita Ku, Tokyo 1140003, Japan

[2] Kitasato Univ, Kitasato Inst Life Sci, Minato Ku, Tokyo 1088641, Japan

来源：

CHEMISTRY LETTERS | 2003年 / 32卷 / 10期

关键词：

D O I：

10.1246/cl.2003.900

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A mild and highly alpha-selective glycosylation of several glycosyl acceptors was performed with an in situ formed glycosyl donor, benzyl-protected glycosyl methyldiphenylphosphonium iodide, to afford the corresponding alpha-disaccharides in high yields in CH2Cl2 at room temperature without any assistance of acid promoters.

引用

收藏

页码：900 / 901

页数：2

相关论文

共 15 条

[1] Stereoselective chemical 1,2-cis O-glycosylation:: From 'sugar ray' to modern techniques of the 21st century [J].

Demchenko, AV .

SYNLETT, 2003, (09) :1225-1240

[2] Glycosyl iodides are highly efficient donors under neutral conditions [J].

Hadd, MJ ;

Gervay, J .

CARBOHYDRATE RESEARCH, 1999, 320 (1-2) :61-69

[3] AN EXTREMELY MILD AND STEREOCONTROLLED CONSTRUCTION OF 1,2-TRANS-BETA-GLYCOSIDIC LINKAGES CAPITALIZING ON BENZYL-PROTECTED GLYCOPYRANOSYL DIETHYL PHOSPHITES AS GLYCOSYL DONORS [J].

HASHIMOTO, S ;

UMEO, K ;

SANO, A ;

WATANABE, N ;

NAKAJIMA, M ;

IKEGAMI, S .

TETRAHEDRON LETTERS, 1995, 36 (13) :2251-2254

[4] Preparation of various carboxylic acid esters from bulky alcohols and carboxylic acids by a new type oxidation-reduction condensation using 2,6-dimethyl-1,4-benzoquinone [J].

Mukaiyama, T ;

Kikuchi, W ;

Shintou, T .

CHEMISTRY LETTERS, 2003, 32 (03) :300-301

[5] Benzylation of carboxylic acids by oxidation-reduction condensation using quinones and benzyloxydiphenylphosphine [J].

Mukaiyama, T ;

Shintou, T ;

Kikuchi, W .

CHEMISTRY LETTERS, 2002, (11) :1126-1127

[6] Glycosyl fluoride - A superb glycosyl donor in glycosylation [J].

Mukaiyama, T ;

Jona, H .

PROCEEDINGS OF THE JAPAN ACADEMY SERIES B-PHYSICAL AND BIOLOGICAL SCIENCES, 2002, 78 (04) :73-83

[7]

Quin L. D, 2000, GUIDE ORGANOPHOSPHOR, P103

[8]

Shimizu M, 1998, SYNTHESIS-STUTTGART, P799

[9]

SHINTOU T, 2003, IN PRESS B CHEM SOC

[10]

SHINTOU T, 2003, IN PRESS CHEM LETT