303127-98-2

Upstream product

• 303127-94-8 Benzyl 4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside 
• 303127-85-7 Methyl 2-O-benzoyl-3,4-di-O-benzyl-1-O-trichloroacetimidoyl-α-D-glucopyrano 
• 100-39-0 benzyl bromide 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 39686-94-7 1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose 
• 303127-80-2 4-Methoxyphenyl 3-O-benzyl-β-D-glucopyranoside 
• 303127-81-3 p-methoxyphenyl 3-O-benzyl-4,6-di-O-benzylidene-β-D-glucopyranoside 
• 303127-79-9 4-Methoxyphenyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranoside 
• 1053708-33-0 N-((2R,3R,4R,5R,6R)-2,5-Bis-benzyloxy-4-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-2,2,2-trichloro-acetamide 
• 303127-87-9 Benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside 
• 303127-88-0 Benzyl 2-deoxy-3,6-di-O-pivaloyl-2-trichloroacetamido-β-D-glucopyranoside 
• 303127-90-4 Benzyl 2-deoxy-3,6-di-O-pivaloyl-2-trichloroacetamido-β-D-galactopyranoside 
• 303127-82-4 4-Methoxyphenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 303127-84-6 Methyl (4-methoxyphenyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosid)uronate 

Downstream Products

• 303128-02-1 Benzyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-2-acetamido-4-O-benzyl-2-deoxy-β-D-galactopyranoside 
• 303128-09-8 (2S,3S,4R,5R,6R)-6-((2R,3R,4R,5R,6R)-3-Acetylamino-2,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-carboxylic acid 
• 303128-00-9 Benzyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-2-acetamido-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-galactopyranoside 

Relevant academic research and scientific papers

Chemical synthesis of β-D-GlcpA(2SO4)-(1→3)-D-GalpNAc(6SO4), the disaccharide repeating unit of shark cartilage chondroitin sulfate D, and of its methyl β-D-glycoside derivative

The syntheses of sodium O-(disodium 2-O-sulfonato-β-D-glucopyranosyluronate)-(1→3)-2-acetamido-2-deoxy-6- O-sulfonato-D-galactopyranose 1, which represents a structural element of shark cartilage chondroitin sulfate D, and of its methyl β-D-glycoside derivative 2 are reported for the first time. The glucuronyl donor 10 is prepared in a straightforward manner from D-glucose, whereas the glycosyl acceptors 20 and 21 are obtained from known 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-1-O-trichloroacetimidoyl- α-D-glucopyranose through glycosylation with benzyl alcohol and methanol, respectively, and subsequent transformation into D-galacto synthons by selective inversion of configuration at C-4. Unexpected pyranose → furanose ring contraction as well as 3,6-anhydro-derivative formation in the D-galacto series are also reported. Stereocontrolled coupling of the imidate 10 with the alcohols 20 and 21 afforded the corresponding β-linked disaccharide derivatives 24 and 25, respectively, which are submitted to radical reduction of the N-trichloroacetyl groups, O-desilylation, saponification, O-sulfonation, and catalytic hydrogenation to provide the target molecules 1 and 2, respectively, in high yields. The Royal Society of Chemistry 2000.