352020-83-8Relevant articles and documents
An efficient synthesis of new 1′-C-methyl-α-O-disaccharides using 1-methylenesugars as the glycosyl donors
Li, Xiaoliu,Ohtake, Hiro,Takahashi, Hideyo,Ikegami, Shiro
, p. 4283 - 4295 (2001)
A series of new 1′-C-methyl-α-disaccharides were firstly synthesized by the directly Lewis acid-catalyzed O-glycosidation of 1-methylenesugars used as glycosyl donors. The O-glycosidation afforded stereospecifically the corresponding 1′-methyl-α-O-glycosides whose configurations were tentatively assigned by the NMR spectra, COSY and the C-H coupling constant 3JH-2′,Me-1′. The O-glycosidation of the acetyl protected 1-methylenesugars showed that the acetyl group at the C-2-O position was not effective to control the stereochemistry of the product by neighboring group participation because of the formation of a tertiary oxycarbenium ion as a stable intermediate.
A facile synthesis of 1′-C-alkyl-α-disaccharides from 1-C-alkyl-hexopyranoses and methyl 1-C-methyl-hexopyranosides
Li, Xiaoliu,Ohtake, Hiro,Takahashi, Hideyo,Ikegami, Shiro
, p. 4297 - 4309 (2007/10/03)
Direct O-glycosidations using the 1-C-alkyl-2,3,4,6-tetra-O-benzyl-hexopyranoses as the glycosyl donors were carried out with a catalytic amount (0.2 equiv.) of trimethylsilyl trifluoromethanesulfonate (TMSOTf). The glycosidations proceeded α-stereoselect