222408-68-6

Basic information

• Product Name: 3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-5,6-O-isopropylidene-D-altritol
• Synonyms: 3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-5,6-O-isopropylidene-D-altritol
• CAS NO: 222408-68-6
• Molecular Weight: 520.741
• Mol File: 222408-68-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-5,6-O-isopropylidene-D-altritol(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-5,6-O-isopropylidene-D-altritol(222408-68-6)
• EPA Substance Registry System: 3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-5,6-O-isopropylidene-D-altritol(222408-68-6)

Safety Data

• Hazardous Substances Data: 222408-68-6(Hazardous Substances Data)

Upstream product

• 107735-20-6 [(dimethylphenylsilyl)methyl]magnesium chloride 
• 103795-16-0 2,3-di-O-benzyl-4,5-O-isopropylidene-D-ribose 
• 7152-47-8 D-ribose diethyl dithioacetal 
• 100-39-0 benzyl bromide 
• 25572-71-8 4,5-O-isopropylidene-D-ribose diethyl dithioacetal 
• 160849-24-1 2,3-di-O-benzyl-4,5-O-isopropylidene-D-ribose diethyl-dithioacetal 

Downstream Products

• 222723-56-0 2-O-acetyl-3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-5,6-di-O-isopropylidene-D-altritol 
• 222723-59-3 2-O-acetyl-3,4-di-O-benzyl-5,6-O-(cyclic sulfate)-1-deoxy-1-dimethylphenylsilyl-D-altritol 
• 222408-70-0 2,5-anhydro-3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-D-altritol 
• 222555-98-8 2,5-anhydro-3,4-di-O-benzyl-D-altritol 
• 222960-53-4 2,5-anhydro-3,4-di-O-benzyl-L-galactitol 
• 102436-29-3 (2R,3R,4S)-3,4-O-dibenzylhex-5-ene-1,2,3,4-tetrol 
• 222408-69-7 3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-D-altritol 

Relevant articles and documents

Preparation of 2,5-anhydrohexitols (part I). Silicon-directed stereocontrolled cyclization

Stereoselective chain-extension of carbohydrate aldehydes with the hydroxymethylating reagent (dimethylphenylsilyl)methylmagnesium chloride (1) followed by acid-mediated cyclization gives access to 2,5-anhydro-hexitols. The stereoselectivity of the ring closure depends on the nature of the acid, i.e., treatment with excess BF3·Et2O or catalytic H2SO4 leads to tetrahydrofurans with 2,3-cis or 2,3-trans configuration, respectively. Concomitant elimination is effectively suppressed in case of cyclisation of the more sterically hindered isopropyl substituted silanes.