HIGHLY STEREOSELECTIVE SYNTHESIS OF BETA-GLYCOSIDES OF 3-DEOXY-2-HEXULOSONATES

被引：13
|
作者：
VLAHOV, IR [1 ]
VLAHOVA, PI [1 ]
SCHMIDT, RR [1 ]
机构：
[1] UNIV CONSTANCE,FAK CHEM,POSTFACH 5560,W-7750 CONSTANCE,GERMANY
来源：
TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 03期
关键词：
D O I：
10.1016/S0957-4166(00)86071-1
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Epsilon-Hydroxy (Z)-enol ethers 6 and 12 were readily prepared from D-glucono-1,5-lactone by ring opening, 2-O-alkylation with triflate 3, and Z-specific beta-elimination. Cyclization of 6 and 12 induced by PhSeBF4 or by PhSeOTf provided exclusively beta-connected disaccharides, which were converted into neuraminic acid analogues 10 and 11 or 3-deoxy-2-glycosyl-D-2-hexulofuranosylonate 13, respectively.
引用
收藏
页码：293 / 296
页数：4
相关论文
共 50 条
  • [1] Highly stereoselective synthesis of 2-deoxy-α-glycosides and α-disaccharides
    Bielawska, H
    Michalska, M
    TETRAHEDRON LETTERS, 1998, 39 (52) : 9761 - 9764
  • [2] A HIGHLY STEREOSELECTIVE SYNTHESIS OF ARYL 2-DEOXY-BETA-GLYCOSIDES VIA THE MITSUNOBU REACTION
    ROUSH, WR
    LIN, XF
    JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20): : 5740 - 5742
  • [3] SYNTHESIS OF ALKYL BETA-GLYCOSIDES
    WEBER, N
    BENNING, H
    CHEMISTRY AND PHYSICS OF LIPIDS, 1982, 31 (04) : 325 - 329
  • [4] SYNTHESIS AND METABOLISM OF ALKYL BETA-GLYCOSIDES
    WEBER, N
    FETTE SEIFEN ANSTRICHMITTEL, 1984, 86 (12): : 585 - 591
  • [5] Stereoselective synthesis of 2-deoxy β-glycosides
    Zhu, Danyang
    Baryal, Kedar N.
    Li, Xiaohua
    Zhu, Jianglong
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
  • [6] SYNTHESIS OF BETA-GLYCOSIDES OF GLYCYRRHETIC ACID
    HIROOKA, M
    MORISHIMA, N
    KAJI, E
    MORI, Y
    ZEN, S
    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1989, 109 (08): : 544 - 559
  • [7] SIMPLE SYNTHESIS OF ACETYLATED STERYL BETA-GLYCOSIDES
    WEBER, N
    CHEMISTRY AND PHYSICS OF LIPIDS, 1977, 18 (02) : 145 - 148
  • [8] FACILE PREPARATION OF BENZYL BETA-GLYCOSIDES OF 2-ACYLAMINO-2-DEOXY-D-GLUCOPYRANOSES
    RHOADS, WD
    GROSS, PH
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1973, B-28 (9-10): : 647 - 649
  • [9] Stereoselective synthesis of triterpene 3-O-2-deoxy-alpha-glycosides
    Baltina, LA
    Flekhter, OB
    Vasiljieva, EV
    MENDELEEV COMMUNICATIONS, 1996, (02) : 63 - 64
  • [10] A highly stereoselective synthesis of 2-deoxy-β-glycosides using 2-deoxy-2-iodo-glucopyranosyl acetate donors
    Roush, WR
    Bennett, CE
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (14) : 3541 - 3542
12345