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

Authors
TOSHIMA K ISHIZUKA T MATSUO G NAKATA M
Citation
K. Toshima et al., ALLYL C-GLYCOSIDATIONS OF TOTALLY UNPROTECTED GLYCALS AND ALLYLTRIMETHYLSILANE WITH TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE (TMSOTF), Tetrahedron letters, 35(31), 1994, pp. 5673-5676
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
31
Year of publication
1994
Pages
5673 - 5676
Database
ISI
SICI code
0040-4039(1994)35:31<5673:ACOTUG>2.0.ZU;2-D
Abstract
Allyl C-glycosidations of the totally unprotected glycals, L-rhamnal ( 1), D-glucal (2), D-galactal (3) and D-fucal (4), with allyltrimethyls ilane (5) using TMSOTf proceeded much more effectively than those of t he corresponding acetylated glycals 10 similar to 13 to furnish the un protected and 2,3-unsaturated allyl alpha-C-glycosides 6 similar to 9 in high yields, respectively.