Improved synthesis of 2,3:4,6-di-O-isopropylidene-D-glucopyranose and -D-galactopyranose

被引:15
|
作者
Gómez, AM [1 ]
Danelón, GO [1 ]
Valverde, S [1 ]
López, JC [1 ]
机构
[1] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
关键词
2,3 : 4,6-Di-O-isopropylidene-D-glucopyranose 2,3 : 4,6-Di-O-isopropylidene-D-galactopyranose; benzyl glycosides; hydrogenolysis; carbohydrate acetals;
D O I
10.1016/S0008-6215(99)00150-0
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
2,3:4,6-Di-O-isopropylidene-D-glucopyranose and -D-galactopyranose acetals are conveniently prepared by hydrogenolysis of benzyl 2,3:4,6-di-O-isopropylidene-beta-D-glucopyranose and -beta-D-galactopyranose in almost quantitative yields in 3 h. This result is in contrast with the sluggish reaction observed (48 h) when the hydrogenolysis was carried out on either anomeric alpha,beta mixtures or on the corresponding a anomers. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:138 / 142
页数:5
相关论文
共 50 条
  • [31] Microscale Synthesis of 2,3:5,6-Di-O-isopropylidene-a-D-mannofur anose (Diacetone Mannose)
    Charonnat, J. A.
    Steinberg, C. S.
    Journal of Chemical Education, 73 (08):
  • [32] 1,2-4,6-DI-O-ISOPROPYLIDENE-D-MANNITOL AND 1,2-3,6-DI-O-ISOPROPYLIDENE-D-MANNITOL
    KUSZMANN, J
    TOMORI, E
    DVORTSAK, P
    CARBOHYDRATE RESEARCH, 1984, 132 (01) : 178 - 183
  • [33] Synthesis of some 6-S-heterocyclic Derivatives of 1,2:3,4-Di-O-isopropylidene-alpha-D-galactopyranose
    Alho, MAM
    DAccorso, NB
    Thiel, IME
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1996, 33 (04) : 1339 - 1343
  • [34] Tetrabutylbis(2,3:4,6-di-isopropylidene-2-keto-L-gulonato)distannoxane
    Dalil, H
    Biesemans, M
    Willem, R
    Gielen, M
    MAIN GROUP METAL CHEMISTRY, 1998, 21 (12): : 741 - 745
  • [35] SYNTHESES OF 3-O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-ALPHA-D-GALACTOPYRANOSE (LACTO-N-BIOSE II) AND 3,4-DI-O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-D-GALACTOPYRANOSE
    AUGE, C
    VEYRIERES, A
    CARBOHYDRATE RESEARCH, 1977, 54 (01) : 45 - 59
  • [36] Mercaptan addition to 1-O-allyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose
    N. N. Sidamonidze
    R. O. Vardiashvili
    M. O. Isakadze
    E. I. Chachua
    Chemistry of Natural Compounds, 2007, 43 : 250 - 252
  • [37] Mercaptan addition to 1-O-allyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose
    Sidamonidze, N. N.
    Vardiashvili, R. O.
    Isakadze, M. O.
    Chachua, E. I.
    CHEMISTRY OF NATURAL COMPOUNDS, 2007, 43 (03) : 250 - 252
  • [38] Polymerizable methacrylate carbohydrate derivatives: 1,2:3,4-di-O-isopropylidene-6-O-methacryloyl-alpha-D-galactopyranose and 1,2:5,6-di-O-isopropylidene-3-O-methacryloly-alpha-D-glucofuranose
    Ojala, WH
    Gleason, WB
    Connelly, MPE
    Wallis, RR
    Kremer, JJ
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1996, 52 : 155 - 158
  • [39] Synthesis of C2-d1-2,3-O-isopropylidene-D-ribose
    Kundu, MK
    Földesi, A
    Chattopadhyaya, J
    CHEMISTRY OF NUCLEIC ACID COMPONENTS, 1999, 2 : 47 - 52
  • [40] Synthesis of 2,3-unsaturated 4-amino sugars and cyclohexyl 2,3-di-O-acetyl-4,6-di-O-methyl-α-D-manno- pyranoside from cyclohexyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
    de Brito, TMB
    da Silva, LP
    Siqueira, VL
    Srivastava, RM
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 1999, 18 (06) : 609 - 616