82598-85-4

Basic information

• Product Name: ethyl (2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)ethanoate
• Synonyms: ethyl (2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)ethanoate
• CAS NO: 82598-85-4
• Molecular Weight: 610.747
• Mol File: 82598-85-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: ethyl (2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)ethanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)ethanoate(82598-85-4)
• EPA Substance Registry System: ethyl (2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)ethanoate(82598-85-4)

Safety Data

• Hazardous Substances Data: 82598-85-4(Hazardous Substances Data)

Upstream product

• 82598-84-3 2,3,4,6-tetra-O-benzyl-D-galactonolactone 
• 6386-24-9 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 214771-14-9 (1(1')-Z)-2,3,4,6-tetra-O-benzyl-1-deoxy-1-(ethoxycarbonyl)methylidene-D-galactopyranose 
• 26954-26-7 ethyl lithioacetate 

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.