303127-99-3

Upstream product

• 1054654-83-9 2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-2-(2,2-dimethyl-propionyloxymethyl)-6-methoxy-5-(2,2,2-trichloro-acetylamino)-3-trifluoromethanesulfonyloxy-tetrahydro-pyran-4-yl ester 
• 303128-06-5 (2S,3S,4S,5R,6S)-5-Benzoyloxy-3,4-bis-benzyloxy-6-(4-methoxy-phenoxy)-tetrahydro-pyran-2-carboxylic acid 
• 303127-83-5 4-Methoxyphenyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranoside 
• 303127-84-6 Methyl (4-methoxyphenyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosid)uronate 
• 303127-82-4 4-Methoxyphenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 303127-93-7 Methyl 4-O-benzyl-2-deoxy-3,6-di-O-pivaloyl-2-trichloroacetamido-β-D-galactopyranoside 
• 303127-79-9 4-Methoxyphenyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranoside 
• 303127-91-5 Methyl 2-deoxy-3,6-di-O-pivaloyl-2-trichloroacetamido-β-D-galactopyranoside 
• 303127-89-1 Methyl 2-deoxy-3,6-di-O-pivaloyl-2-trichloroacetamido-β-D-glucopyranoside 
• 303127-81-3 p-methoxyphenyl 3-O-benzyl-4,6-di-O-benzylidene-β-D-glucopyranoside 
• 1054629-48-9 N-((2R,3R,4R,5R,6R)-5-Benzyloxy-4-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-2,2,2-trichloro-acetamide 
• 303127-80-2 4-Methoxyphenyl 3-O-benzyl-β-D-glucopyranoside 
• 39686-94-7 1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose 
• 56644-73-6 Methyl 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside 

Downstream Products

• 303128-03-2 Methyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosylunorate)-(1->3)-2-acetamido-4-O-benzyl-2-deoxy-β-D-galactopyranoside 
• 303128-10-1 (2S,3S,4R,5R,6R)-6-((2R,3R,4R,5R,6R)-3-Acetylamino-5-benzyloxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yloxy)-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-carboxylic acid 
• 303128-01-0 Methyl 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.