273400-80-9

Upstream product

• 3282-30-2 pivaloyl chloride 
• 273400-79-6 4-methoxyphenyl 2-deoxy-2-trichloroacetamido-β-D-glucopyranoside 
• 150-76-5 4-methoxy-phenol 
• 56644-75-8 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroacetamido)-β-D-glucopyranose 
• 273400-77-4 4-methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside 

Downstream Products

• 273400-86-5 4-methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside 
• 428865-83-2 4-methoxyphenyl (methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-β-D-glucopyranosyluronate)-(1->3)-4-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside 
• 428865-85-4 4-methoxyphenyl (methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-β-D-glucopyranosyluronate)-(1->3)-6-O-benzoyl-4-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside 
• 428865-84-3 4-methoxyphenyl (methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-β-D-glucopyranosyluronate)-(1->3)-4-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside 
• 428865-81-0 4-methoxyphenyl 4-O-benzyl-2-deoxy-3,6-di-O-pivaloyl-2-trichloroacetamido-β-D-galactopyranoside 
• 428865-82-1 4-methoxyphenyl 4-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside 
• 273400-81-0 4-methoxyphenyl 2-deoxy-3,6-di-O-pivaloyl-2-trichloroacetamido-β-D-galactopyranoside 
• 428866-00-6 N-[(2S,3R,4R,5R,6R)-5-Benzyloxy-4-hydroxy-6-hydroxymethyl-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl]-2,2,2-trichloro-acetamide 
• 273400-82-1 4-methoxyphenyl 2-deoxy-2-trichloroacetamido-β-D-galactopyranoside 

Relevant academic research and scientific papers

Unexpected stereochemical outcome of activated 4,6-O-benzylidene derivatives of the 2-deoxy-2-trichloroacetamido-D-galacto series in glycosylation reactions during the synthesis of a chondroitin 6-sulfate trisaccharide methyl glycoside

The synthesis of methyl (β-D-glucopyranosyluronic acid)-(1→3)-(2-acetamido-2-deoxy-6-O-sulfonato-β-D-galactopyranosyl)-(1→4)-(β-D-glucopyranosid)uronate trisodium salt, a chondroitin 6-sulfate trisaccharide derivative, is described. Loss of stereocontrol in glycosylation reactions involving activated 4,6-O-benzylidene derivatives of the 2-deoxy-2-trichloroacetamido-D-galacto series and D-glucuronic acid-derived acceptors was highlighted. This drawback was overcome through the use of phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-trichloroacetamido-β-D-galactopyranoside, which afforded the desired β-linked disaccharide derivative in high yield with an excellent stereoselectivity. This later was submitted to acid-catalyzed methanolysis, followed by benzylidenation, and condensed with methyl 2,3,4-tri-O-benzoyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate to afford the expected trisaccharide derivative. Subsequent transformation of the N-trichloroacetyl group into N-acetyl, mild acid hydrolysis, selective O-sulfonation at C-6 of the amino sugar moiety, and saponification afforded the target molecule as its sodium salt in high yield. Copyright (C) 2000 Elsevier Science Ltd.