SYNTHESIS OF METHYL 2,6-DIDEOXY-4-THIO-ALPHA-D-RIBO-HEXOPYRANOSIDE (METHYL 4-THIODIGITOXOSIDE) - A CONSTITUENT OF THE CALICHEAMICINS AND ESPERAMICINS

被引：0
|
作者：
CLASSEN, A
SCHARF, HD
机构：
来源：
LIEBIGS ANNALEN DER CHEMIE | 1993年 / 02期
关键词：
HEMITHIOACETALS; DEOXY; CALICHEAMICINS; ESPERAMICINS; THIODIGITOXOSIDE; DIGITOXOSIDE; 4-THIO-; ANTIBIOTICS; ANTITUMOR; ANTITUMOR ANTIBIOTICS; SACCHARIDES; CARBOHYDRATES;
D O I：
暂无
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The 4-thio analog of 2,6-dideoxy-D-ribo-hexopyranose (D-digitoxose) is part of the saccharide chain of the calicheamicins and esperamicins. A straightforeward synthesis of the 4-thiodigitoxoside 12 as its diacetate 13 starting from methyl alpha-D-galactopyranoside (1) is described. Properties and structure of 13 are presented.
引用
收藏
页码：183 / 187
页数：5
相关论文
共 50 条
  • [41] LIPOMYCINS, .3. ISOLATION AND IDENTIFICATION OF METHYL 2,6-DIDEOXY-D-RIBO-HEXOSIDES
    ZEECK, A
    ANNALEN DER CHEMIE-JUSTUS LIEBIG, 1975, (11): : 2079 - 2088
  • [42] STRUCTURE OF METHYL 4-O-BENZOYL-6-BROMO-3-TOSYL-2,6-DIDEOXY-BETA-D-ARABINO-HEXOPYRANOSIDE
    JEDRZEJAS, MJ
    BAKER, RJ
    BINKLEY, RW
    TOWNS, RLR
    ADAIR, N
    ANDRAS, M
    ANWARI, F
    CHEN, ZH
    HUFF, R
    LIU, XG
    MARTUCH, R
    SKLADANY, M
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1993, 49 : 481 - 483
  • [43] SYNTHESIS AND SEROLOGICAL PROPERTIES OF METHYL 2,6-DIDEOXY-4-O-ME-ALPHA-D AND L- ARABINO-HEXOPYRANOSIDE PRESENT IN THE GLYCOLIPID PHENOLIC ANTIGEN OF MYCOBACTERIUM-KANSASII
    GILLERON, M
    FOURNIE, JJ
    POUGNY, JR
    PUZO, G
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 1988, 7 (04) : 733 - 748
  • [44] SYNTHESIS OF METHYL 3-AMINO-3,4-DIDEOXY-ALPHA-D-XYLO-HEXOPYRANOSIDE AND 3-AMINO-3,4-DIDEOXY-BETA-D-XYLO-HEXOPYRANOSIDE
    MARTIN, A
    MONNERET, C
    GAUTIER, C
    FOURNIER, JP
    ROGER, P
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 1990, 9 (06) : 853 - 861
  • [45] Studies of the synthesis of rubranitrose and crystal structure of methyl 2,3,6-trideoxy-3-C-methyl-3-nitro-alpha-D-ribo-hexopyranoside
    Ye, H
    Noecker, L
    Boyko, WJ
    Giuliano, RM
    Yap, GPA
    Rheingold, AL
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 1997, 16 (03) : 373 - 383
  • [46] DISPLACEMENT OF SUGAR CHLOROSULFATES BY BROMIDE, AZIDE, AND ACETATE - CONVENIENT SYNTHESIS OF METHYL 3,6-DIDEOXY-BETA-D-RIBO-HEXOPYRANOSIDE
    BUNDLE, DR
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (11): : 2751 - 2755
  • [47] SYNTHESIS OF METHYL 2,3-ANHYDRO-4-DEOXY-6-O-METHYL-ALPHA-DL-LYXO-HEXOPYRANOSIDE
    SWEET, F
    BROWN, RK
    CANADIAN JOURNAL OF CHEMISTRY, 1968, 46 (13): : 2283 - &
  • [48] DEOXYSUGAR SYNTHESIS .2. DEOXYGENATIONS OF METHYL 2,6-DIBENZYLOXYCARBONYLAMINO-2,6-DIDEOXY-ALPHA-D-GLUCOPYRANOSIDE
    SAEKI, H
    TAKEDA, N
    SHIMADA, Y
    OHKI, E
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1976, 24 (04) : 724 - 730
  • [49] IDENTIFICATION OF VARIOSE AS 2,6-DIDEOXY-3-O-METHYL-D-RIBO-HEXOSE (D-CYMAROSE)
    BRIMACOMBE, JS
    ALHASAN, Z
    MENGECH, AS
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (08): : 1800 - 1803
  • [50] NOVEL ROUTE TO 4-THIOFURANOSIDES - SYNTHESIS OF METHYL 4-THIO-ALPHA-D-TALOFURANOSIDE
    CLASSON, B
    GAREGG, PJ
    SAMUELSSON, B
    LIU, ZC
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 1987, 6 (04) : 593 - 597
12345