99881-07-9

Basic information

• Product Name: (2R,3S,4S)-5,6-Bis-(phenyl-hydrazono)-hexane-2,3,4-triol
• CAS NO: 99881-07-9
• Molecular Weight: 342.398
• Mol File: 99881-07-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3S,4S)-5,6-Bis-(phenyl-hydrazono)-hexane-2,3,4-triol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4S)-5,6-Bis-(phenyl-hydrazono)-hexane-2,3,4-triol(99881-07-9)
• EPA Substance Registry System: (2R,3S,4S)-5,6-Bis-(phenyl-hydrazono)-hexane-2,3,4-triol(99881-07-9)

Safety Data

• Hazardous Substances Data: 99881-07-9(Hazardous Substances Data)

Upstream product

• 84985-25-1 6-deoxy-L-mannose 
• 100-63-0 phenylhydrazine 
• 634-74-2 6-deoxy-D-glucose 
• 18545-94-3 6-deoxy-L-xylo-hexulose 
• 29217-83-2 6-deoxy-L-gulono-1,4-lactone 
• 634-74-2 6-deoxy-D-gulose 
• 7658-08-4 D-quionovose 
• 59-88-1 phenylhydrazine hydrochloride 
• 64364-07-4 6-deoxy-D-talose 
• 35867-45-9 6-deoxy-L-glucose 
• 3615-41-6 L-Rhamnose 
• 18039-26-4 2,3,4-tri-O-benzyl-D-xylopyranose 
• 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 

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