273400-77-4

Upstream product

• 56644-75-8 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroacetamido)-β-D-glucopyranose 
• 150-76-5 4-methoxy-phenol 
• 925673-04-7 2-amino-2-deoxy-1,3,4,6-tetra-O-(trimethylsilyl)-α-D-glucopyranose 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 

Downstream Products

• 273400-79-6 4-methoxyphenyl 2-deoxy-2-trichloroacetamido-β-D-glucopyranoside 
• 1616860-27-5 4-methoxyphenyl 4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside 
• 273400-80-9 4-methoxyphenyl 2-deoxy-3,6-di-O-pivaloyl-2-trichloroacetamido-β-D-glucopyranoside 
• 273400-86-5 4-methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside 
• 273400-82-1 4-methoxyphenyl 2-deoxy-2-trichloroacetamido-β-D-galactopyranoside 
• 321380-47-6 methyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl)-(1->4)-(methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)uronate 
• 321380-51-2 methyl (2-acetamido-4-O-acetyl-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-(methyl 2-O-benzoyl-3-O-benzyl-α-L-idopyranosid)uronate 
• 321380-67-0 (2R,3S,4R,5R,6R)-3-((2S,3R,4R,5R,6R)-3-Acetylamino-4-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid 
• 321380-43-2 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-1-O-trichloroacetimidoyl-α-D-galactopyranose 
• 321380-41-0 4-methoxyphenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside 
• 321380-39-6 4-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside 
• 321380-37-4 4-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside 
• 321380-35-2 4-methoxyphenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside 
• 321380-33-0 4-methoxyphenyl 4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside 

Relevant academic research and scientific papers

Selective Acetylation of Non-anomeric Groups of per- O-Trimethylsilylated Sugars

Selective modification of the hydroxyl groups of sugars has been a long-standing challenge due to their proximate relative reactivity. Herein, we report a TMSOTf-catalyzed selective acetylation of the non-anomeric hydroxyl groups of several per-O-TMS-protected sugar substrates while leaving their anomeric group unaffected. In addition to standing versatile by itself, the anomeric O-TMS group left intact can be functionalized to afford key sugar precursors such as imidate donors, which could otherwise be synthesized via a stepwise anomeric deprotection-functionalization procedure.

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.