236739-66-5

Basic information

• Product Name: ethyl acetoxy(1-acetoxy-2,3,4,6-tetra-O-benzyl-D-galactopyranosyl)ethanoate
• Synonyms: ethyl acetoxy(1-acetoxy-2,3,4,6-tetra-O-benzyl-D-galactopyranosyl)ethanoate
• CAS NO: 236739-66-5
• Molecular Weight: 726.821
• Mol File: 236739-66-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: ethyl acetoxy(1-acetoxy-2,3,4,6-tetra-O-benzyl-D-galactopyranosyl)ethanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl acetoxy(1-acetoxy-2,3,4,6-tetra-O-benzyl-D-galactopyranosyl)ethanoate(236739-66-5)
• EPA Substance Registry System: ethyl acetoxy(1-acetoxy-2,3,4,6-tetra-O-benzyl-D-galactopyranosyl)ethanoate(236739-66-5)

Safety Data

• Hazardous Substances Data: 236739-66-5(Hazardous Substances Data)

Upstream product

• 214771-14-9 (1(1')-Z)-2,3,4,6-tetra-O-benzyl-1-deoxy-1-(ethoxycarbonyl)methylidene-D-galactopyranose 
• 82598-84-3 2,3,4,6-tetra-O-benzyl-D-galactonolactone 
• 6386-24-9 2,3,4,6-tetra-O-benzyl-D-galactopyranose 

Relevant articles and documents

Alkylidenation of sugar lactones and further transformation to C-glycosides

The Wittig reaction of (carbethoxymethylene)triphenylphosphorane with perbenzylated sugar δ-lactones and their 2-acetamido-2-deoxy derivatives is described. It is shown that this olefination occurred readily with the galacto and gluco derivatives, leading stereoselectively to Z-C-glycosylidenes in good yields. However, the same reaction with the perbenzylated 2-deoxy-D-arabino-hexono-1,5-lactone and the mannonolactones worked poorly. Reduction over Pd/C followed by acetylation of the obtained C-glycosylidenes led stereoselectively to peracetylated β-C-glycosides and amino β-C-glycosides. The olefin function could also be reduced selectively by Raney nickel or NiCl2/NaBH4, affording the perbenzylated C-glycosides and amino β-C-glycosides. Other transformation of the enol ether function is also reported.