34693-27-1

Basic information

• Product Name: (3aR,6S,6aR)-6-hydroxy-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxole
• Synonyms: (3aR,6S,6aR)-6-hydroxy-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxole
• CAS NO: 34693-27-1
• Molecular Weight: 160.17
• Mol File: 34693-27-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (3aR,6S,6aR)-6-hydroxy-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxole(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,6S,6aR)-6-hydroxy-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxole(34693-27-1)
• EPA Substance Registry System: (3aR,6S,6aR)-6-hydroxy-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxole(34693-27-1)

Safety Data

• Hazardous Substances Data: 34693-27-1(Hazardous Substances Data)

Upstream product

• 29884-67-1 (4R,5S)-1,2,4,5,6-Pentahydroxy-hexan-3-one 
• 67-64-1 acetone 
• 917108-76-0 5-O-phthalimido-1,2-O-isopropylidene-α-D-xylofuranose 

Downstream Products

• 34560-62-8 1,2-O-isopropylidene-5-(O-benzyl)-α-D-apio-D-furanose 
• 1333503-47-1 (3aR,6S,6aR)-6-(4-methoxybenzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxole 
• 76768-64-4 (3aR,6S,6aR)-6-(benzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxole 
• 34339-66-7 1,2-O-isopropylidene-3-C-<(benzyloxy)methyl>-α-D-threo-furanose 
• 14048-38-5 (3aR,6aR)-2,2-dimethyl-6-methylenetetrahydrofuro[2,3-d][1,3]dioxole 
• 681811-41-6 (-)-(3aR,6S,6aR)-6-benzyloxymethyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole 
• 681811-48-3 (-)-(3aR,6R,6aR)-6-benzyloxymethyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole 
• 95-44-3 L-threose 
• 123487-68-3 C₁₄H₁₈N₂O₅S 
• 1293981-99-3 1,2-O-isopropylidene-3-O-benzoyl-(E)-3-(diethylphosphono)allyl-α-D-erythrofuranose 
• 1293981-90-4 1,2-O-isopropylidene-3-O-benzoyl-(E)-3-(diethylphosphono)vinyl-α-D-erythrofuranose 
• 1293981-85-7 1,2-O-isopropylidene-3-O-benzoyl-3-vinyl-α-D-erythrofuranose 
• 139348-81-5 C₂₀H₂₇NO₅S 
• 139348-80-4 C₂₀H₂₇NO₅S 

Relevant articles and documents

Beneficial effect of internal hydrogen bonding interactions on the β-fragmentation of primary alkoxyl radicals. Two-step conversion of D-xylo- and D-ribofuranoses into L-threose and D-erythrose, respectively

(Chemical Equation Presented) Primary alkoxyl free radicals were generated from their readily synthesized N-phthalimido derivatives under reductive conditions. Primary alkoxyl radicals derived from their corresponding xylo- and ribofuranose derivatives underwent, exclusively, an unusual β-fragmentation affording L-threose and D-erythrose derivatives, respectively. This occurs because the alkoxyl radical is capable of achieving an internal hydrogen-bonding interaction leading to a stable six-membered ring intramolecular hydrogen-bonded structure. When the hydroxyl group is protected, the β-fragmentation pathway is prevented and the hydrogen atom transfer (HAT) pathway occurs. Computational studies provided strong support for the experimental observations.