Further Anomeric Esters
3.3
533
Ogawa and coworkers reported that trimethylsilyl trifluoromethanesulfonate (TMSOTf)
was a very effective promoter for the glycosylation of a glycerolipid alcohol with octaO-acetyl-β-lactose [23] and with 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranose [24] to synthesize model glycoglycerolipids ( > Scheme 18). However, glycosylations with glycosyl acetates in the presence of TMSOTf sometimes accompany side reactions
such as transfer of an acyl group from the glycosyl donor to the glycosyl acceptor [25],
⊡ Scheme 18
(Ref. [23,24])
⊡ Scheme 19
(Ref. [28])
3.3
533
Ogawa and coworkers reported that trimethylsilyl trifluoromethanesulfonate (TMSOTf)
was a very effective promoter for the glycosylation of a glycerolipid alcohol with octaO-acetyl-β-lactose [23] and with 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranose [24] to synthesize model glycoglycerolipids ( > Scheme 18). However, glycosylations with glycosyl acetates in the presence of TMSOTf sometimes accompany side reactions
such as transfer of an acyl group from the glycosyl donor to the glycosyl acceptor [25],
⊡ Scheme 18
(Ref. [23,24])
⊡ Scheme 19
(Ref. [28])