38184-16-6

Basic information

• Product Name: phenyl O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside
• CAS NO: 38184-16-6
• Molecular Weight: 1017.25
• Mol File: 38184-16-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: phenyl O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside(38184-16-6)
• EPA Substance Registry System: phenyl O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside(38184-16-6)

Safety Data

• Hazardous Substances Data: 38184-16-6(Hazardous Substances Data)

Upstream product

• 498-07-7 levoglucosan 
• 120403-27-2 phenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside 
• 10548-46-6 1,6-anhydro-2,3,4-tri-O-benzyl-β-D-glucopyranose 
• 100-44-7 benzyl chloride 
• 120403-26-1 phenyl 2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 120403-32-9 phenyl O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 87470-73-3 phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 120444-53-3 6-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranosyl chloride 
• 4356-78-9 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl chloride 

Downstream Products

• 120403-32-9 phenyl O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside 

Relevant articles and documents

SYSTEMATIC CHEMICAL SYNTHESIS AND N.M.R. SPECTRA OF METHYL α-GLYCOSIDES OF ISOMALTO-OLIGOSACCHARIDES AND RELATED COMPOUNDS

Acid-catalyzed thiophenolysis of 1,6-anhydro-2,3,4-tri-O-benzyl-β-D-glucopyranose and acetylation of the resulting phenyl 2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside (4) gave phenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside (5).Reaction of 5 with chlorine gave, stereospecifically, the corresponding β-glycosyl chloride, which was treated with 4 in the presence of silver perchlorate and 2,4,6-trimethylpyridine to afford phenyl O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside (17).Crystalline O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D- glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranosyl chloride, readily obtainable in a stereospecific manner from 17 by treatment with chlorine, was used as the key glycosyl (isomaltosyl) donor in the bockwise synthesis of methyl glycosides of isomalto-oligosaccharides, up to and including the octasaccharide.The methyl α-glycoside of isomaltotetraose fluorinated at C-6 of the terminal D glucopyranosyl group was prepared by using SnCl2-activated 2,3,4-tri-O-benzyl-6-deoxy-6-fluoro-α,β-D-glucopyranosyl fluoride as the glycosyl donor, a suitably protected methyl α-isomaltotrioside as the nucleophile, and silver perchlorate as the promoter.The n.m.r. spectra (1H- and 13C-) of numereous synthetic intermediates were analyzed and completely assigned by a variety of two-dimensional homo- and hetero-nuclear n.m.r.-spectroscopic techniques, and the final deprotected title oligosaccharides were characterized by 13C-n.m.r. data.Silver perchlorate-mediated glycosylation reactions involving β-glycosyl chlorides were high-yielding and showed high stereoselectivity for the formation of an α-(cis)-glycosidic linkage.The practical limitation of obtaining high isomalto-oligosaccharides in this way appears to lie solely in the separation technique applied for the resolution of the crude products formed.