77453-66-8

Basic information

• Product Name: 3,4,5-tri-O-benzyl-1-deoxy-α-D-sorbopyranose
• CAS NO: 77453-66-8
• Molecular Weight: 434.532
• Mol File: 77453-66-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3,4,5-tri-O-benzyl-1-deoxy-α-D-sorbopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5-tri-O-benzyl-1-deoxy-α-D-sorbopyranose(77453-66-8)
• EPA Substance Registry System: 3,4,5-tri-O-benzyl-1-deoxy-α-D-sorbopyranose(77453-66-8)

Safety Data

• Hazardous Substances Data: 77453-66-8(Hazardous Substances Data)

Upstream product

• 87-72-9 D-Xylose 
• 242143-00-6 methyl 2,3,4-tri-O-benzyl-D-xylopyranoside 
• 18039-26-4 2,3,4-tri-O-benzyl-D-xylopyranose 
• 91-09-8 methyl xyloside 
• 77453-63-5 2,3,4-tri-O-benzyl-6-deoxy-D-iditol 

Downstream Products

• 33639-75-7 2,3,4-tri-O-benzyl-6-deoxy-D-idopyranose 
• 2079-46-1 (2R,3S,4S)-5,6-Bis-(phenyl-hydrazono)-hexane-2,3,4-triol 
• 77453-65-7 2,3,4-tri-O-benzyl-6-deoxy-D-idono-1,5-lactone 
• 77453-63-5 2,3,4-tri-O-benzyl-6-deoxy-D-iditol 

Relevant articles and documents

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