303127-79-9

Usage

Uses

Used in Carbohydrate Chemistry:
4-Methoxyphenyl 2,4,6-tri-o-acetyl-3-o-benzyl-beta-D-glucopyranoside is used as a carbohydrate building block for the synthesis of complex carbohydrate structures. Its unique structure allows for the formation of various glycosidic linkages, making it a valuable tool in the development of new carbohydrate-based compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Methoxyphenyl 2,4,6-tri-o-acetyl-3-o-benzyl-beta-D-glucopyranoside is used as an intermediate in the synthesis of biologically active compounds. Its ability to form stable glycosidic linkages with other molecules makes it a promising candidate for the development of new drugs with improved pharmacological properties.
Used in Synthesis of β-D-GlcpA(2SO4)-(1 →3)-D-GalpNAc(6SO4):
4-Methoxyphenyl 2,4,6-tri-o-acetyl-3-o-benzyl-beta-D-glucopyranoside is specifically used in the synthesis of β-D-GlcpA(2SO4)-(1 →3)-D-GalpNAc(6SO4), the disaccharide repeating unit of shark cartilage. This disaccharide unit is an important component of shark cartilage, which has been studied for its potential therapeutic applications, such as its antiangiogenic and anticancer properties.

InChI:InChI=1/C26H30O10/c1-16(27)31-15-22-23(33-17(2)28)24(32-14-19-8-6-5-7-9-19)25(34-18(3)29)26(36-22)35-21-12-10-20(30-4)11-13-21/h5-13,22-26H,14-15H2,1-4H3/t22-,23-,24+,25-,26-/m1/s1

Upstream product

• 150-76-5 4-methoxy-phenol 
• 39686-94-7 1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose 

Downstream Products

• 303127-80-2 4-Methoxyphenyl 3-O-benzyl-β-D-glucopyranoside 
• 303127-98-2 Benzyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside 
• 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 
• 303127-99-3 Methyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside 
• 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 
• 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 
• 303128-03-2 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 
• 303127-85-7 Methyl 2-O-benzoyl-3,4-di-O-benzyl-1-O-trichloroacetimidoyl-α-D-glucopyrano 
• 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 

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.