ALLYL C-GLYCOSIDATIONS OF TOTALLY UNPROTECTED GLYCALS AND ALLYLTRIMETHYLSILANE WITH TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE (TMSOTF)

被引:26
作者
TOSHIMA, K
ISHIZUKA, T
MATSUO, G
NAKATA, M
机构
[1] Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Kohoku-ku, Yokohama, 223
关键词
D O I
10.1016/S0040-4039(00)77276-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Allyl C-glycosidations of the totally unprotected glycals, L-rhamnal (1), D-glucal (2), D-galactal (3) and D-fucal (4), with allyltrimethylsilane (5) using TMSOTf proceeded much more effectively than those of the corresponding acetylated glycals 10 similar to 13 to furnish the unprotected and 2,3-unsaturated allyl alpha-C-glycosides 6 similar to 9 in high yields, respectively.
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页码:5673 / 5676
页数:4
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