Oligosaccharide synthesis based on glycosyl donors and acceptors carrying phosphorus-containing leaving groups

被引：23
|
作者：
Hashimoto, S [1 ]
Sakamoto, H [1 ]
Honda, T [1 ]
Ikegami, S [1 ]
机构：
[1] TEIKYO UNIV,FAC PHARMACEUT SCI,SAGAMIKO,KANAGAWA 19901,JAPAN
来源：
TETRAHEDRON LETTERS | 1997年 / 38卷 / 29期
关键词：
D O I：
10.1016/S0040-4039(97)01122-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Efficient synthetic strategy for oligosaccharides has been developed by exploiting the difference in anomeric reactivity between glycosyl donors and accepters carrying phosphorus-containing leaving groups, wherein the tetramethylphosphoroamidate group plays a pivotal role as anomeric protective group as well as leaving group. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码：5181 / 5184
页数：4
相关论文
共 50 条
  • [1] Chemoselective glycosidation strategy based on glycosyl donors and acceptors carrying phosphorus-containing leaving groups:: a convergent synthesis of ganglioside GM3
    Sakamoto, H
    Nakamura, S
    Tsuda, T
    Hashimoto, S
    TETRAHEDRON LETTERS, 2000, 41 (40) : 7691 - 7695
  • [2] Armed-disarmed glycosidation strategy based on glycosyl donors and acceptors carrying phosphoroamidate as a leaving group: A convergent synthesis of globotriaosylceramide
    Hashimoto, S
    Sakamoto, H
    Honda, T
    Abe, H
    Nakamura, S
    Ikegami, S
    TETRAHEDRON LETTERS, 1997, 38 (52) : 8969 - 8972
  • [3] NOVEL GLYCOSIDATION METHODOLOGY - THE USE OF PHENYL SELENOGLYCOSIDES AS GLYCOSYL DONORS AND ACCEPTORS IN OLIGOSACCHARIDE SYNTHESIS
    MEHTA, S
    PINTO, BM
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (12): : 3269 - 3276
  • [4] HIGHLY SELECTIVE GLYCOSIDATION REACTIONS CAPITALIZING ON PHOSPHORUS-CONTAINING LEAVING GROUPS
    HASHIMOTO, S
    HONDA, T
    YANAGIYA, Y
    NAKAJIMA, M
    IKEGAMI, S
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1995, 53 (07) : 620 - 632
  • [5] THE USE OF THIOGLYCOSIDES AS GLYCOSYL DONORS IN OLIGOSACCHARIDE SYNTHESIS
    SILWANIS, BA
    DASGUPTA, F
    GAREGG, PJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1988, 195 : 92 - CARB
  • [6] DISPIROKETALS IN SYNTHESIS .5. A NEW OPPORTUNITY FOR OLIGOSACCHARIDE SYNTHESIS USING DIFFERENTIALLY ACTIVATED GLYCOSYL DONORS AND ACCEPTORS
    BOONS, GJ
    GRICE, P
    LESLIE, R
    LEY, SV
    YEUNG, LL
    TETRAHEDRON LETTERS, 1993, 34 (52) : 8523 - 8526
  • [7] Glycosyl Donors with Phosphorimidate Leaving Groups for Either a- or a-Glycosidation
    Tetrahedron Lett, 35 (6139):
  • [8] Novel glycosyl donors for enzyme-catalyzed oligosaccharide synthesis
    Shoda, Shin-ichiro
    Tanaka, Tomonari
    Noguchi, Masato
    Kobayashi, Atsushi
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 237
  • [9] SYNTHESIS OF PHOSPHORUS-CONTAINING HETEROCYCLES
    BHATIA, MS
    DEVI, S
    JINDAL, R
    KAUR, B
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1988, 65 (04) : 275 - 276
  • [10] DEVELOPMENT OF THE USE OF THIOGLYCOSIDES AS GLYCOSYL DONORS IN GLYCOSIDE AND OLIGOSACCHARIDE SYNTHESIS
    GAREGG, PJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 209 : 78 - CARB
12345