126797-39-5Relevant academic research and scientific papers
The Synthesis and Reactivity of Cyclic Thiocarbonates Derived from Some Carbohydrate 1,2-Diols
Patroni, Joseph J.,Stick, Robert V.,Tilbrook, D. Matthew G.,Skelton, Brian W.,White, Allan H.
, p. 2127 - 2141 (2007/10/02)
The attempted synthesis of several carbohydrate 1,2-diols is reported, together with the transformation of two of these diols into cyclic thiocarbonates, namely 4,6-O-benzylidene-3-O-methyl-1,2-O-thiocarbonyl-α-D-glucose and 3,4-O-isopropylidene-1,2-O-thiocarbonyl-β-D-arabinose.The treatment of these thiocarbonates, and a furanose 1,2-thiocarbonate previously prepared by Mukaiyama, with methyl halides and with tributyltin hydride is discussed.A single-crystal X-ray diffraction study of 3,4-O-isopropylidene-1,2-O)-thiocarbonyl-β-D-arabinose is recorded.
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.
