EFFICIENT SYNTHESES OF D-PSICO-FURANOSES AND D-SORBO-FURANOSES

被引:14
作者
FAIVREBUET, V
EYNARD, I
NGA, HN
DESCOTES, G
GROUILLER, A
机构
[1] Universite Lyon I, Laboratoire de Chimie Organique II, Villeurbanne
关键词
D O I
10.1080/07328309308018995
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
D-Psico- and D-sorbo-furanosyl derivatives 3 and 6 were synthesized in two steps through the methylenation of the D-ribono- and D-xylono-lactones 1 and 4 with dicyclopentadienyldimethyltitanium, followed by the cis-dihydroxylation of the resultant olefins 2 and 5 with catalytic osmium tetroxide and 4-methylmorpholine N-oxide.
引用
收藏
页码:349 / 356
页数:8
相关论文
共 24 条
  • [1] DESOXYNITRO SUGARS .3. SYNTHESIS OF KETOSES BY CHAIN ELONGATION OF 1-DEOXY-1-NITROALDOSES - NUCLEOPHILIC ADDITIONS AND SOLVOLYSIS OF NITRO ETHERS
    AEBISCHER, B
    BIERI, JH
    PREWO, R
    VASELLA, A
    [J]. HELVETICA CHIMICA ACTA, 1982, 65 (07) : 2251 - 2272
  • [2] TITANIUM-MEDIATED METHYLENE TRANSFER-REACTIONS ON SUGAR ESTERS, LACTONES, AND ULOSES
    ALI, MH
    COLLINS, PM
    OVEREND, WG
    [J]. CARBOHYDRATE RESEARCH, 1990, 205 : 428 - 434
  • [3] SYNTHESIS OF PARTIALLY-PROTECTED D-FRUCTOFURANOSES AND D-FRUCTOSE-6-PHOSPHATES
    AYRALKALOUSTIAN, S
    FLOYD, MB
    [J]. CARBOHYDRATE RESEARCH, 1991, 214 (01) : 187 - 192
  • [4] SYNTHESIS OF 3-DEOXY-3-FLUORO-D-FRUCTOSE
    BOLS, M
    SZAREK, WA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (05) : 445 - 446
  • [5] INSITU PREPARATION OF (MU-CHLORO)(MU-METHYLENE)BIS(CYCLOPENTADIENYL)(DI-METHYLALUMINUM)TITANIUM (TEBBE REAGENT)
    CANNIZZO, LF
    GRUBBS, RH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (13) : 2386 - 2387
  • [6] METHYLENATION OF ALDONOLACTONES
    CSUK, R
    GLANZER, BI
    [J]. TETRAHEDRON, 1991, 47 (09) : 1655 - 1664
  • [7] SYNTHESIS OF 1'-DEOXYPSICOFURANOSYL-DEOXYNUCLEOSIDES AS POTENTIAL ANTI-HIV AGENTS
    FAIVREBUET, V
    GROUILLER, A
    DESCOTES, G
    [J]. NUCLEOSIDES & NUCLEOTIDES, 1992, 11 (07): : 1411 - 1424
  • [8] FAIVREBUET V, 1992, NUCLEOSIDES NUCLEOTI
  • [9] A NOVEL STEREOSPECIFIC SYNTHESIS OF 5-AMINO-1-BETA-D-FRUCTOFURANOSYLIMIDAZOLE-4-CARBOXAMIDE
    GROUILLER, A
    MACKENZIE, G
    NAJIB, B
    SHAW, G
    EWING, D
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (10) : 671 - 672
  • [10] GROUILLER A, 1988, NUCLEOS NUCLEOT, V7, P675