An efficient diastereoselective synthesis of β-1-formyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside

被引:20
|
作者
Labéguère, F [1 ]
Lavergne, JP [1 ]
Martinez, J [1 ]
机构
[1] Univ Montpellier 2, CNRS, UMR 5810, Lab Aminoacides Peptides & Prot, F-34095 Montpellier 5, France
关键词
D O I
10.1016/S0040-4039(02)01477-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A diastereoselective synthesis of beta-1-formyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside in four steps, using an umpolung Seebach reaction is described. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7271 / 7272
页数:2
相关论文
共 50 条
  • [31] A NEW SYNTHESIS OF 2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSYLIDENE ACETALS, USING TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE AS THE CATALYST
    HORITO, S
    ASANO, K
    UMEMURA, K
    HASHIMOTO, H
    YOSHIMURA, J
    CARBOHYDRATE RESEARCH, 1983, 121 (SEP) : 175 - 185
  • [32] SYNTHESIS AND STEREOCHEMISTRY OF 2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSYLIDENE ACETALS OF ALPHA-DIOLS AND MONOSACCHARIDES
    TAMARU, M
    HORITO, S
    YOSHIMURA, J
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1980, 53 (12) : 3687 - 3690
  • [33] SYNTHESIS OF 2,3,4,6-TETRA-O-ACYL-BETA-D-GLUCOPYRANOSYL-1-PHOSPHATES
    VOITENKO, AV
    VOLKOVA, LV
    EVSTIGNEEVA, RP
    ZHURNAL OBSHCHEI KHIMII, 1980, 50 (09): : 2140 - 2141
  • [34] Structural study of 2,3,4,6-tetra(O-vinyl) methyl-α-D-glucopyranoside
    Trofimov, B. A.
    Oparina, L. A.
    Krivdin, L. B.
    Gusarova, N. K.
    Chernyshev, K. A.
    Sinegovskaya, L. M.
    Klyba, L. V.
    Parshina, L. N.
    Tantsyrev, A. P.
    Kazheva, O. N.
    Alexandrov, G. G.
    D'yachenko, O. A.
    JOURNAL OF MOLECULAR STRUCTURE, 2006, 791 (1-3) : 1 - 9
  • [35] EFFICIENT SYNTHESIS OF S-(2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOSYL) AND SE-(2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOSYL) THIOPHOSPHATES AND SELENOPHOSPHATES
    LIPKA, P
    MICHALSKA, M
    CARBOHYDRATE RESEARCH, 1983, 113 (02) : 317 - 320
  • [36] N-acetyl-2,3,4,6-tetra-O-acetyl-N-benzyl-β-D-glucopyranosylamine
    Dianez, Maria Jesus
    Estrada, Maria Dolores
    Lopez-Castro, Amparo
    Perez-Garrido, Simeon
    Acta Crystallographica, Section C: Crystal Structure Communications, 1997, 53 (pt 3): : 378 - 379
  • [37] N-acetyl-2,3,4,6-tetra-O-acetyl-N-benzyl-beta-D-glucopyranosylamine
    Dianez, MJ
    Estrada, MD
    LopezCastro, A
    PerezGarrido, S
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1997, 53 : 378 - 379
  • [38] METHYL 2,3,4,6-TETRA-O-(4-METHOXYBENZYL)-1-THIO-BETA-D-GLUCOPYRANOSIDE - A NOVEL REAGENT FOR ALPHA-GLYCOSYLATION TOWARDS NITROPHENYL OR BENZYL GLYCOSIDES
    JAIN, RK
    MATTA, KL
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (12) : 1707 - 1712
  • [39] AN IMPROVED SYNTHESIS OF BENZYL 2-ACETAMIDO-4-O-(2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSYL)-6-O-BENZYL-2-DEOXY-ALPHA-D-GALACTOPYRANOSIDE
    BOVIN, NV
    KORCHAGINA, EY
    KHORLIN, AY
    BIOORGANICHESKAYA KHIMIYA, 1985, 11 (09): : 1253 - 1255
  • [40] Synthesis of 2,3,4,6-tetra-O-acetyl-β-D-gluco(galacto)pyranosylcaprolactams and 2,3,4,6-tetra-O-acetyl-β-D-gluco(galacto) pyranosylpyrrolidones
    N. N. Sidamonidze
    L. K. Janiashvili
    R. O. Vardiashvili
    R. A. Gakhokidze
    Chemistry of Natural Compounds, 2006, 42 : 127 - 128