74831-27-9Relevant academic research and scientific papers
Preparation of Sugars with Branched Chains, a Methylene Bridge, or C-1-Phenyl Substituents by the Ramirez Dioxaphosphole Condensation
David, Serge,Lepine, Marie-Christine
, p. 1262 - 1266 (2007/10/02)
The products of condensation of 2,3-O-isopropylidene-D-glyceraldehyde with 4,5-dimethyl- and 4,5-tetramethylene-2,2,2-trimethoxy-1,3,2-dioxaphospholes, (1) and (2), were hydrolysed to the free sugars which were converted by acidified methanol into the corresponding mixture of glycosides.In this way were prepared the methylpyranosides and furanosides of 1-deoxy-3-C-methyl-D-ribo-hexose, and 1,2-C-tetramethylene-D-ribose .Condensation of the same aldehyde with the 4-phenyldioxaphosphole (3) led to 1-C-phenyl-D-lyxose (15) which was further characterized as the tetra-O-benzoate (16) and tetra-O-acetate (17) of the α-D-pyranoside tautomer.
