612845-04-2

Basic information

• Product Name: 3-O-benzyl-1,2-O-isopropylidene-6-O-triisopropylsilyl-α-D-glucopyranoside
• Synonyms: 3-O-benzyl-1,2-O-isopropylidene-6-O-triisopropylsilyl-α-D-glucopyranoside
• CAS NO: 612845-04-2
• Molecular Weight: 466.69
• Mol File: 612845-04-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-O-benzyl-1,2-O-isopropylidene-6-O-triisopropylsilyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-benzyl-1,2-O-isopropylidene-6-O-triisopropylsilyl-α-D-glucopyranoside(612845-04-2)
• EPA Substance Registry System: 3-O-benzyl-1,2-O-isopropylidene-6-O-triisopropylsilyl-α-D-glucopyranoside(612845-04-2)

Safety Data

• Hazardous Substances Data: 612845-04-2(Hazardous Substances Data)

Upstream product

• 2873-29-2 D-glucal triacetate 
• 13265-84-4 D-glucal 
• 137915-37-8 1,2-dideoxy-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose 
• 67-64-1 acetone 
• 356067-93-1 3-O-benzyl-6-O-triisopropylsilyl-D-glucal 

Downstream Products

• 444118-41-6 methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosiduronate 
• 210100-63-3 (3aR,5R,6R,7S,7aR)-7-Benzyloxy-5-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-ol 

Relevant articles and documents

One-pot conversion of glycals to cis-1,2-isopropylidene-α-glycosides

Described is a general method for the conversion of glycals to the corresponding 1,2-cis-isopropylidene-α-glycosides. Epoxidation of glycals with dimethyldioxirane followed by ZnCl2-catalyzed addition of acetone converted a variety of protected glycals into 1,2-cis-isopropylidene-α-glycosides in good yield. The reaction is compatible with a range of protecting groups, including esters, benzyl ethers, and silyl ethers, as well as free hydroxyl groups. This method has been applied to develop a synthesis of protected glucuronic acid 1, a key intermediate in the synthesis of glycosaminoglycans. Compound 1 was produced in seven steps and 32% overall yield.