CYCLIZATION OF HYDROXY ENOL ETHERS - A STEREOCONTROLLED APPROACH TO 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID CONTAINING DISACCHARIDES

被引：37
|
作者：
HAUDRECHY, A
SINAY, P
机构：
[1] Laboratoire de Chimie, U.R.A. 1110, Ecole Normale Supérieure, 75231 Paris Cidex 05
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 15期
关键词：
D O I：
10.1021/jo00041a017
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A method for the preparation of the carboxylic acids 14 and 15 has been developed, starting from known 2,3,5,6-di-O-isopropylidene-D-mannofuranose. Esterification of 14 and 15 with methanol, methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranoside, and 1,2,5,6-di-O-isopropylidene-alpha-D-glucofuranose, followed by reaction with Tebbe reagent and selective deprotection gave, respectively, the key complex hydroxy enol ethers 20, 26, and 35. Stereoselective iodocyclization, followed by transformation of the CH2I appendage into a methyloxycarbonyl group, gave the corresponding protected KDO-containing disaccharides.
引用
收藏
页码：4142 / 4151
页数：10
相关论文
共 50 条
  • [1] A STEREOCONTROLLED APPROACH TO 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID CONTAINING DISACCHARIDES
    HAUDRECHY, A
    SINAY, P
    TETRAHEDRON LETTERS, 1990, 31 (40) : 5765 - 5768
  • [2] NEW STEREOCONTROLLED APPROACH TO 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID CONTAINING DISACCHARIDES
    PAQUET, F
    SINAY, P
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (26) : 8313 - 8315
  • [3] NOVEL DISACCHARIDES CONTAINING 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO) AND LIPID A SUBUNIT ANALOGS
    KISO, M
    FUJITA, M
    HAYASHI, E
    HASEGAWA, A
    UNGER, FM
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 1987, 6 (04) : 691 - 696
  • [4] SYNTHESIS OF 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO)
    FRICK, W
    KRULLE, T
    SCHMIDT, RR
    LIEBIGS ANNALEN DER CHEMIE, 1991, (05): : 435 - 438
  • [5] LOCALIZATION OF THE ENZYME 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID ALDOLASE
    KNAPPMANN, BR
    KULA, MR
    APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 1990, 33 (03) : 324 - 329
  • [6] MONOSACCHARIDE CHEMISTRY OF 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO)
    UNGER, FM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1981, 182 (AUG): : 39 - CARB
  • [7] A NEW SYNTHESIS OF 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO)
    COUTROT, P
    GRISON, C
    TABYAOUI, M
    TETRAHEDRON LETTERS, 1993, 34 (32) : 5089 - 5092
  • [8] IODONIUM ION PROMOTED CYCLIZATION - A CONVENIENT APPROACH TO GLYCOSYL DONORS OF 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO)
    VANDERKLEIN, PAM
    BOONS, GJPH
    VEENEMAN, GH
    VANDERMAREL, GA
    VANBOOM, JH
    SYNLETT, 1990, (06) : 311 - 313
  • [9] BUILDING UNITS OF OLIGOSACCHARIDES .52. SYNTHESIS OF DISACCHARIDES CONTAINING 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO) AND D-GLUCOSAMINE
    PAULSEN, H
    HAYAUCHI, Y
    UNGER, FM
    LIEBIGS ANNALEN DER CHEMIE, 1984, (07): : 1270 - 1287
  • [10] DO ENDOTOXINS DEVOID OF 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID EXIST
    CAROFF, M
    LEBBAR, S
    SZABO, L
    BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1987, 143 (03) : 845 - 847
12345