2079-46-1

Upstream product

• 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 
• 73-34-7 6-deoxy-D-idose 
• 100-63-0 phenylhydrazine 
• 91-09-8 methyl xyloside 
• 242143-00-6 methyl 2,3,4-tri-O-benzyl-D-xylopyranoside 
• 33639-75-7 2,3,4-tri-O-benzyl-6-deoxy-D-idopyranose 
• 77453-63-5 2,3,4-tri-O-benzyl-6-deoxy-D-iditol 
• 77453-66-8 3,4,5-tri-O-benzyl-1-deoxy-α-D-sorbopyranose 
• 18039-26-4 2,3,4-tri-O-benzyl-D-xylopyranose 
• 87-72-9 D-Xylose 

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