183371-82-6

Basic information

• Product Name: (3aR,3bS,5R,6S,6aR,7aR)-2,2-Dimethyl-5-phenyl-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxole-5,6-diol
• Synonyms: (3aR,3bS,5R,6S,6aR,7aR)-2,2-Dimethyl-5-phenyl-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxole-5,6-diol
• CAS NO: 183371-82-6
• Molecular Weight: 294.304
• Mol File: 183371-82-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3aR,3bS,5R,6S,6aR,7aR)-2,2-Dimethyl-5-phenyl-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxole-5,6-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,3bS,5R,6S,6aR,7aR)-2,2-Dimethyl-5-phenyl-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxole-5,6-diol(183371-82-6)
• EPA Substance Registry System: (3aR,3bS,5R,6S,6aR,7aR)-2,2-Dimethyl-5-phenyl-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxole-5,6-diol(183371-82-6)

Safety Data

• Hazardous Substances Data: 183371-82-6(Hazardous Substances Data)

Upstream product

• 3067-56-9 D-glucurono-3,6-lactone acetonide 
• 126214-81-1 5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D glucofuraurono-6,3-lactone 
• 591-51-5 phenyllithium 

Downstream Products

• 183371-85-9 (1R,2R)-1-((3aR,5R,6S,6aR)-6-Hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-phenyl-ethane-1,2-diol 
• 183371-84-8 (1R,2S)-1-((3aR,5R,6S,6aR)-6-Hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-phenyl-ethane-1,2-diol 

Relevant articles and documents

The first example of a 6-C-aryl-D-glucose: Inhibition of glucokinase

The synthesis of the epimeric 6-C-phenylglucoses is reported; these are the first compounds with one of the prochiral methylene hydrogens on C-6 of a hexose being replaced by an aryl group. Both isomers inhibit glucokinase and provide further indications that 6-C-alkyl- and 6-C-aryl-carbohydrates may provide a new range of sugar mimics that control enzymes associated with formation, hydrolysis and other fates of sugar-6-phosphates. X-ray crystal structures of 6-C-phenyl-L-glycero-β-D-gluco-hexopyranose and (2R,3S,4R,6R,7R,8S)2,3,6,7-tetrahydroxy-6,7-O-isopropylidene-1,5-oxa-2 -phenyl-bicyclo-[3.3.0]octane are reported.