116523-62-7Relevant articles and documents
The Selective Monobenzylidenation of Some Monosaccharides and Their Derivatives with α,α-Dimethoxytoluene
Patroni, Joseph J.,Stick, Robert V.,Skelton, Brian W.,White, Allan H.
, p. 91 - 102 (2007/10/02)
The treatment of some monosaccharides and their derivatives with α,α-dimethoxytoluene and an acid catalyst in dimethylformamide at about 80 deg C can lead to selective benzylidenation, e.g. methyl α-D-mannopyranoside gives mainly methyl 4,6-O-benzylidene-α-D-mannoside, together with two other minor monobenzylidene derivatives (2,3-) and two minor dibenzylidene derivatives (2,3:4,6-).The treatment of various other pyranoses and pyranosides is also described.As well, a 1H n.m.r. study of the acid transformation of some of the above α-D-mannosides is reported, together with a single-crystal X-ray diffraction structure determination of a novel monobenzylidene derivative, namely methyl (S)-2,3-O-benzylidene-α-D-mannopyranoside.