R. Ghosh, D. De, B. Shown
Sep 15, 1999
Citations
0
Influential Citations
29
Citations
Journal
Carbohydrate Research
Abstract
Abstract InCl 3 has been used for the first time as a mediator for the C-glycosylation of per- O -acetylglycals with allyltrimethylsilane, and the reactions proceeded to give products in good-to-excellent yield and in high diastereoselectivity. The 1,5-anti diastereoselectivity in the allylation of 3,4,6-tri- O -acetyl-1,5-anhydro-2-deoxy- d - arabino -hex-1-enitol and 3,4-di- O -acetyl-1,5-anhydro-2,6-dideoxy- l - arabino -hex-1-enitol and the 1,4-anti diastereoselectivity with 3,4-di- O -acetyl-1,5-anhydro-2-deoxy- d - erythro -pent-1-enitol are in the range 80–90%, whereas 3,4,6-tri- O -acetyl-1,5-anhydro-2-deoxy- d - lyxo -hex-1-enitol furnished exclusively the corresponding C -α- d -galactopyranosyl compound.