88095-32-3

Basic information

• Product Name: (4aR,8aS)-6-Methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine
• CAS NO: 88095-32-3
• Molecular Weight: 232.279
• Mol File: 88095-32-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (4aR,8aS)-6-Methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine(CAS DataBase Reference)
• NIST Chemistry Reference: (4aR,8aS)-6-Methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine(88095-32-3)
• EPA Substance Registry System: (4aR,8aS)-6-Methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine(88095-32-3)

Safety Data

• Hazardous Substances Data: 88095-32-3(Hazardous Substances Data)

Upstream product

• 75-16-1 methylmagnesium bromide 
• 88095-31-2 1,5-anhydro-4,6-O-benzylidene-2-deoxy-3-O-mesyl-D-ribo-hex-1-enitol 
• 124314-05-2 1,5-anhydro-4,6-O-benzylidene-2-deoxy-3-O-(2,4,6-triisopropylbenzenesulfonyl)-D-ribo-hex-1-enitol 
• 5987-33-7 4,6-O-benzylidene-D-allal 
• 14125-70-3 1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-arabino-hex-1-enitol 
• 917-64-6 methyl magnesium iodide 

Relevant articles and documents

Stereoselective synthesis of a C-glycosylic compound (a "methyl C-glycoside") through a regioselective free-radical ring-opening reaction. A single-crystal X-ray structure determination

Readily available 3,4,6-tri-O-acetyl-D-glucal was converted to 2,6-anhydro-5,7-O-benzylidene-1,3,4-trideoxy-D-arabino-hept-3-enitol, a methyl C-glycosylic compound. Cyclopropanation of 4,6-O-benzylidene-D-glucal, followed by tributylstannyl radical-mediated regioselective ring opening of the 1,2-cyclopropano sugar led to a 2,6-anhydro-1-deoxyheptose, (a "methyl C-β-D-glycoside"). The stereochemistry of the 1,2-cyclopropano sugar and the "methyl C-glycoside" were confirmed by single-crystal X-ray diffraction studies.

REACTION OF 4,6-O-BENZYLIDENE-3-O-MESYL-ALLAL WITH ALLYLIC GRIGNARD REAGENTS. HIGHLY REGIO- AND STEREOSELECTIVE PREPARATION OF 2,6-DISUBSTITUTED DIHYDROPYRAN RINGS

The reaction of 4,6-O-benzylidene-1,2-dideoxy-3-O-mesyl-D-ribo-hex-1-enopyranose reacted with 2-propenylmagnesium chloride or 2-methyl-2-propenylmagnesium chloride to give 1,5-anhydro-4,6-O-benzylidene-2,3-dideoxy-1-C-prop-2-enyl- (or 2-methylprop-2-enyl)-β-D-erythro-hex-2-enitol in good yield.