119093-27-5Relevant academic research and scientific papers
An Improvement in the Preparation of Some Carbohydrate Benzylidene Acetals
Ferro, Vito,Mocerino, Mauro,Stick, Robert V.,Tilbrook, D. Matthew G.
, p. 813 - 815 (1988)
Carbohydrate benzylidene and p-methoxybenzylidene acetals are easily prepared by treatment of various sugar derivatives with either benzaldehyde diethyl acetal or p-methoxybenzaldehyde diethyl acetal, respectively, in refluxing chloroform containing camph
The Synthesis of Some Pyrrolidines as Potential Precursors to Retronecine
Ferro, Vito,Skelton, Brian W.,Stick, Robert V.,White, Allan H.
, p. 787 - 803 (2007/10/02)
Methyl β-D-galactopyranoside was converted into methyl 4-azido-3-O-benzyl-6-O-t-butyldiphenylsilyl-2,4-dideoxy-β-D-arabino-hexoside, but subsequent transformation of the anomeric centre into a dithioacetal was unsatisfactory. Alternatively, methyl β-D-galactopyranoside easily gave methyl 4-azido-3,6-di-O-benzyl-2,4-dideoxy-β-D-arabino-hexoside, and this could be transformed by a reductive amination into two pyrrolidines as potential precursors to retronecine. Related chemistry gave (4S,5S,6R)-6-benzyloxy-4-benzyloxymethyl-3-oxa-1-azabicyclooctan-2-one, the structure of which was confirmed by a single-crystal X-ray structure determination. Finally, the synthesis of a potential precursor to heliotridine (an epimer of retronecine), namely methyl 4-azido-3-O-benzyl-6-O-t-butyldiphenylsilyl-2,4-dideoxy-α-D-ribo-hexoside, from methyl α-D-mannopyranoside is reported.
