55123-31-4

Upstream product

• 59-23-4 D-Galactose 
• 108-24-7 acetic anhydride 
• 543-80-6 barium(II) acetate 
• 64-19-7 acetic acid 
• 4451-36-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride 
• 563-63-3 silver(I) acetate 
• 10257-28-0 D-Galactose 

Downstream Products

• 282088-49-7 phenyl 2,3,5,6-tetra-O-acetyl-β-D-selenogalactofuranoside 
• 39698-24-3 tetra-O-acetyl-β-D-galactofuranosyl bromide 
• 4451-36-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride 
• 6919-96-6 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 100645-44-1 p-nitrophenyl 2,3,5,6-tetra-O-acetyl-β-D-galactofuranoside 
• 207131-41-7 phenyl 2,3,5,6-tetra-O-acetyl-1-thio-β-D-galactofuranoside 
• 284030-03-1 phenyl 2,3,5,6-tetra-O-benzyl-1-thio-β-D-glucofuranoside 
• 53829-44-0 (2R,3R,4R)-2-((R)-1,2-Dihydroxy-ethyl)-5-phenylsulfanyl-tetrahydro-furan-3,4-diol 

Relevant academic research and scientific papers

Synthesis of immunostimulatory α- C -galactosylceramide glycolipids via sonogashira coupling, asymmetric epoxidation, and trichloroacetimidate- mediated epoxide opening

Stereocontrolled syntheses of α-C-GalCer (2) and its α-C-acetylenic analogue 6 were accomplished in high efficiency by a convergent construction strategy from 1-hexadecene and d-galactose. The key transformations include Sonogashira coupling, Sharpless asymmetric epoxidation, and Et2AlCl-catalyzed cyclization of an epoxytrichloroacetimidate to generate protected dihydrooxazine 21.

The influence of boric acid on the acetylation of aldoses: 'One-pot' syntheses of penta-O-acetyl-β-D-glucofuranose and its crystalline propanoyl analogue

When glucose and boric acid are heated in acetic acid a soluble compound forms from which, with acetic anhydride and catalytic amounts of sulfuric acid, a mixture consisting of >90% of the glucofuranose per-acetates (α : β ratio 1 : 1.8) is obtained in high yield. In the absence of the sulfuric acid partial acetylation takes place and penta-O-acetyl-β-D-glucofuranose (α: β ratio 1 : 52) is obtainable in good yield by removal of boric acid and completion of the esterification by addition of acetic anhydride and pyridine. A new, crystalline glucofuranose, penta-O-propanoyl-β-D-glucofuranose, is obtained in 58% yield in a 'one-pot' procedure using boric acid. The effects of boric acid on the acid-catalysed acetylation of other aldo-hexoses and -pentoses suggest that the synthesis of furanosyl per-esters could be successful with xylose and idose as well as with glucose.

H-Beta zeolite as an efficient catalyst for per-O-acetylation of mono- and disaccharides

Among the six different zeolites examined, H-beta is demonstrated to be a highly efficient and selective catalyst for the per-O-acetylation of various mono-and disaccharides and methyl glycosides.