Diastereoselective synthesis of β-(3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-N-tert-butoxycarbonyl-D-alanine

被引：18

作者：

Lieberknecht, A

Griesser, H

Krämer, B

Bravo, RD

Colinas, PA

Grigera, RJ

机构：

[1] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany

[2] Natl Univ La Plata, Fac Ciencias Exactas, Lab Estudio Compuestos Organ, RA-1900 La Plata, Argentina

[3] Natl Univ La Plata, Fac Ciencias Exactas, Inst Fis Liquidos & Sistemas Biol, RA-1900 La Plata, Argentina

来源：

TETRAHEDRON | 1999年 / 55卷 / 21期

关键词：

D O I：

10.1016/S0040-4020(99)00306-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Key steps in the synthesis of beta-(3,4,6-tri-O-benzyl-2-deoxy-beta-D-galactopyranosyl)-N-tert-butoxycarbonyl-D-alanine are the Wittig reaction of 2-deoxy-galactopyranosylphosphonium salt 2 and Garner aldehyde, as well as the subsequent diastereoselective hydrogenation of the olefinated sugar 3a,b. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：6475 / 6482

页数：8

共 49 条

[1] SYNTHESIS OF MAJOR HISTOCOMPATIBILITY COMPLEX CLASS-I BINDING GLYCOPEPTIDES
ARSEQUELL, G
HAURUM, JS
ELLIOTT, T
DWEK, RA
LELLOUCH, AC
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (13): : 1739 - 1745
[2] Remote asymmetric induction:: Synthesis of C-linked α-galactoserine and homoserine derivatives by electrophilic amination
Arya, P
Ben, RN
Qin, HP
[J]. TETRAHEDRON LETTERS, 1998, 39 (34) : 6131 - 6134
[3] DIASTEREOSELECTIVE RADICAL-ADDITION TO METHYLENEOXAZOLIDINONES - AN ENANTIOSELECTIVE ROUTE TO ALPHA-AMINO-ACIDS
AXON, JR
BECKWITH, ALJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (05) : 549 - 550
[4] Stereoselective synthesis of carbon-linked analogues of α- and β-galactoserine glycoconjugates using asymmetric enolate methodology
Ben, RN
Orellana, A
Arya, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (14) : 4817 - 4820
[5] SYNTHESIS OF CARBON-LINKED GLYCOPEPTIDES AS STABLE GLYCOPEPTIDE MODELS
BERTOZZI, CR
HOEPRICH, PD
BEDNARSKI, MD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) : 6092 - 6094
[6] CARBON-LINKED GALACTOSPHINGOLIPID ANALOGS BIND SPECIFICALLY TO HIV-1 GP120
BERTOZZI, CR
COOK, DG
KOBERTZ, WR
GONZALEZSCARANO, F
BEDNARSKI, MD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (26) : 10639 - 10641
[7] DIRECT PREPARATION OF 2-DEOXY-D-GLUCOPYRANOSIDES FROM GLUCALS WITHOUT FERRIER REARRANGEMENT
BOLITT, V
MIOSKOWSKI, C
LEE, SG
FALCK, JR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (23) : 5812 - 5813
[8] RESEARCHES ON ACETYLENIC COMPOUNDS .1. THE PREPARATION OF ACETYLENIC KETONES BY OXIDATION OF ACETYLENIC CARBINOLS AND GLYCOLS
BOWDEN, K
HEILBRON, IM
JONES, ERH
WEEDON, BCL
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1946, (JAN): : 39 - 45
[9] Stereoselective synthesis of a C-glycosidic analog of N-glucoasparagine
Burkhart, F
Hoffmann, M
Kessler, H
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (11): : 1191 - 1192
[10] BURKHART F, 1997, ANGEW CHEM, V109, P1240

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