18608-91-8

Upstream product

• 4348-84-9 6-deoxy D-allose 
• 100-63-0 phenylhydrazine 
• 4926-05-0 2,3-isopropylidene-L-rhamnose 
• 69515-54-4 (2R,3S,4S)-2-methyl-3,4-dihydro-2H-pyran-3,4-diol 
• 634-74-2 6-deoxy-D-gulose 
• 20031-16-7 6-deoxy-D-gulono-1,4-lactone 
• 4152-79-8 1,2-O-isopropylidene-5-methyl-5-deoxy-α-D-xylofuranose 
• 50600-39-0 5-deoxy-5-iodo-1,2-O-isopropylidene-alpha-D-xylofuranose 
• 7658-08-4 D-quionovose 
• 59-88-1 phenylhydrazine hydrochloride 
• 2438-80-4 L-Fucose 
• 72358-76-0 phenylhydrazine acetate 
• 7658-10-8 6-Deoxy-L-talose 
• 645-50-1 rhamnose-phenylhydrazone 

Relevant academic research and scientific papers

Highly Stereoselective Grignard Reaction of an Aldopyranose: A Simple Synthesis of 6-Deoxy-D-idose from D-Xylose

Grignard reaction of 2,3,4-tri-O-benzyl-D-xylopyranose yielded a single product with very high stereoselectivity.A threo relationship of the newly created chiral center with respect to C2 was established by converting the product into the δ-lactone of D-ido configuration, then to the unsaturated lactone of threo configuration.The result made possible a stereoselective synthesis of 6-deoxy-D-idose from D-xylose in a small number of steps.Models accounting for the high stereoselectivity in the Grignard reaction of aldoses are discussed.Keywords - Grignard reaction; stereoselectivity; configuration of unsaturated lactones; 2,3,4-tri-O-benzyl-D-xylose; 1-deoxy-D-sorbose; 6-deoxy-D-iono-1,5-lactone; 6-deoxy-D-idose; stereocontrol models