Literature DB >> 3621237

Total synthesis of sialosylcerebroside, GM4.

M Numata, M Sugimoto, K Koike, T Ogawa.   

Abstract

Described are total syntheses of O-[sodium (5-acetamido-3,5-dideoxy-D -glycero-alpha-D-galacto-2-nonulopyranosyl)onate]-(2----3)-O -beta-D -galactopyranosyl-(1----1)-(2R,3S,4E)-2-N-tetracosanoylsphingen ine,O-[sodium (5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosyl+ ++)onate] -(2----3)-O-alpha-D-galactopyranosyl-(1----1)-(2R,3S,4E)-2-N -tetracosanoylsphingenine, O-[sodium (5-acetamido-3,5-dideoxy-D-glycero-beta -D-galacto-2-nonulopyranosyl)onate]-(2----3)-O-beta-D-gal act opyranosyl -(1----1)-(2R,3S,4E)-2-N-tetracosanoylsphingenine, and O-[sodium (5-acetamido-3,5-dideoxy-D-glycero-beta-D-galacto-2-nonulopyranosyl++ +)onate] -(2----3)-O-alpha-D-galactopyranosyl-(1----1)-(2R,3S,4E)-2-N -tetracosanoylsphingenine by using O-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D -galacto-2-nonulopyranosyl)onate]-(2----3)-2,3,4,6-tetra-O-a cetyl-D -galactopyrano-syl trichloroacetimidate and O-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-beta -D-galacto-2-nonulopyranosyl)onate]-(2----3)-2,4,6-tri-O-ace tyl-D-galactopyranosyl trichloroacetimidate as key glycosyl donors, and (2S,3R,4E)-3 -O-benzoyl-2-N-tetracosanoylsphingenine as a key glycosyl acceptor.

Entities:  

Mesh:

Substances:

Year:  1987        PMID: 3621237     DOI: 10.1016/0008-6215(87)80182-9

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN: 0008-6215            Impact factor:   2.104


  5 in total

1.  Palladium(II)-catalyzed enantioselective synthesis of 2-vinyl oxygen heterocycles.

Authors:  Jeffrey S Cannon; Angela C Olson; Larry E Overman; Nicole S Solomon
Journal:  J Org Chem       Date:  2012-02-08       Impact factor: 4.354

2.  Synthesis of chemically modified sialic acid-containing sialyl-LeX ganglioside analogues recognized by the selectin family.

Authors:  M Yoshida; A Uchimura; M Kiso; A Hasegawa
Journal:  Glycoconj J       Date:  1993-02       Impact factor: 2.916

3.  Mechanism of the cobalt oxazoline palladacycle (COP)-catalyzed asymmetric synthesis of allylic esters.

Authors:  Jeffrey S Cannon; Stefan F Kirsch; Larry E Overman; Helen F Sneddon
Journal:  J Am Chem Soc       Date:  2010-11-03       Impact factor: 15.419

Review 4.  First principles insight into the alpha-glucan structures of starch: their synthesis, conformation, and hydration.

Authors:  Iben Damager; Søren Balling Engelsen; Andreas Blennow; Birger Lindberg Møller; Mohammed Saddik Motawia
Journal:  Chem Rev       Date:  2010-04-14       Impact factor: 60.622

5.  Synthesis of deoxygalactose-containing sialyl Le(X) ganglioside analogues to elucidate the structure necessary for selectin recognition.

Authors:  S Komba; H Ishida; M Kiso; A Hasegawa
Journal:  Glycoconj J       Date:  1996-04       Impact factor: 2.916

  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.