201139-13-1Relevant academic research and scientific papers
Chemoselective glycosidation strategy based on glycosyl donors and acceptors carrying phosphorus-containing leaving groups: A convergent synthesis of ganglioside GM3
Sakamoto,Nakamura,Tsuda,Hashimoto
, p. 7691 - 7695 (2007/10/03)
A convergent synthesis of ganglioside GM3 has been achieved by capitalizing on three different phosphorus-containing leaving groups, in which the key features involve a chemo- and regioselective α-glycosidation of sialyl phosphite with partially benzylated galactosyl tetramethylphosphorodiamidate by the aid of trifluoromethanesulfonic acid and a traditionally uncommon coupling of an α-sialyl-(2→3)- galactosyl donor with a glucosylceramide building block which has the β-O-linked ceramide prebuilt into the glucose by a diphenyl phosphate method. (C) 2000 Elsevier Science Ltd.
'Armed-disarmed' glycosidation strategy based on glycosyl donors and acceptors carrying phosphoroamidate as a leaving group: A convergent synthesis of globotriaosylceramide
Hashimoto, Shun-Ichi,Sakamoto, Hiroki,Honda, Takeshi,Abe, Hiroshi,Nakamura, Sei-Ichi,Ikegami, Shiro
, p. 8969 - 8972 (2007/10/03)
A stereocontrolled synthesis of globotriaosylceramide with three different glycosidic linkages has been accomplished by linear and convergent routes exploiting 'armed-disarmed' glycosidation methodology based on glycosyl donors and acceptors carrying tetramethylphosphoroamidate as a leaving group. In particular, the convergent strategy featuring a coupling of a galactosyl(1→4)-galactosyl donor with a glucosylceramide derivative has proven to be extremely efficient.
