Stereospecific uncatalyzed α-O-glycosylation and α-C-glycosidation by means of a new D-gulal-derived α vinyl oxirane

被引:37
作者
Di Bussolo, V [1 ]
Caselli, M [1 ]
Romano, MR [1 ]
Pineschi, M [1 ]
Crotti, P [1 ]
机构
[1] Univ Pisa, Dipartimento Chim Bioorgan & Biofarm, I-56126 Pisa, Italy
关键词
D O I
10.1021/jo0491152
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of alpha vinyl oxirane 5, prepared through a new route to the D-gulal system, with O-nucleophiles (alcohols and di-O-isopropylidene-alpha-D-monosaccharides) and C-nucleophiles (lithium alkyls) affords, in a completely stereoselective way, the corresponding 2-unsaturated alpha O- and C-glycosides having the same configuration as the starting epoxide.
引用
收藏
页码:7383 / 7386
页数:4
相关论文
共 11 条
  • [1] STEREOSELECTIVE TOTAL SYNTHESIS OF METHYL ALPHA-D-GLUCOPYRANOSIDES AND ALPHA-L-GLUCOPYRANOSIDES
    ACHMATOWICZ, O
    BIELSKI, R
    [J]. CARBOHYDRATE RESEARCH, 1977, 55 (MAY) : 165 - 176
  • [2] New stereoselective β-C-glycosidation by uncatalyzed 1,4-addition of organolithium reagents to a glycal-derived vinyl oxirane
    Di Bussolo, V
    Caselli, M
    Pineschi, M
    Crotti, P
    [J]. ORGANIC LETTERS, 2003, 5 (12) : 2173 - 2176
  • [3] New stereoselective β-glycosylation via a vinyl oxirane derived from D-glucal
    Di Bussolo, V
    Caselli, M
    Pineschi, M
    Crotti, P
    [J]. ORGANIC LETTERS, 2002, 4 (21) : 3695 - 3698
  • [4] Engstrom KM, 2001, ANGEW CHEM INT EDIT, V40, P1128, DOI 10.1002/1521-3773(20010316)40:6<1128::AID-ANIE11280>3.3.CO
  • [5] 2-A
  • [6] Ferrier R. J., 2004, ORG REACTIONS, V62, P569, DOI DOI 10.1002/0471264180.OR062.04
  • [7] Ferrier RJ, 2001, TOP CURR CHEM, V215, P153
  • [8] Stereoselective palladium-catalyzed O-glycosylation using glycals
    Kim, H
    Men, H
    Lee, C
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (05) : 1336 - 1337
  • [9] EFFICIENT PREPARATION OF INTERMEDIATES CORRESPONDING TO C22-C27 AND C28-C34 OF FK-506
    LINDE, RG
    EGBERTSON, M
    COLEMAN, RS
    JONES, AB
    DANISHEFSKY, SJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) : 2771 - 2776
  • [10] Takhi M, 2001, SYNLETT, P427