Synthesis of silylallene glycosides and diene diglycosides by C-glycosidation of D-glucal with 1,4-bis(trimethylsilyl)-2-butyne.
[reaction: see text] Silylmethylallenyl glycosides, symmetrical and unsymmetrical diene glycosides, were synthesized by C-glycosidation with 1,4-bis(trimethylsilyl)-2-butyne in good yield. The nature of the product is controlled by the choice of Lewis acid, BF(3).OEt(2), or SnCl(4). The efficient construction of unsymmetrical diene glycosides was achieved in one pot on the basis of the order of addition of sugar starting materials.
Saeeng
Rungnapha
R
Department of Chemistry, Faculty of Science, Burapha University, Sangsook, Chonburi 20131, Thailand. rungnaph@buu.ac.th
Isobe
Minoru
M
D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D006027:Glycosides; D012821:Silanes