p-methylphenyl 3,6-di-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-deoxy-1-thio-α-D-glucopyranoside

Base Information

• Chemical Name: p-methylphenyl 3,6-di-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-deoxy-1-thio-α-D-glucopyranoside
• CAS No.: 1423497-54-4
• Molecular Formula: C₅₄H₅₈O₈S
• Molecular Weight: 867.116

Synonyms:p-methylphenyl 3,6-di-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-deoxy-1-thio-α-D-glucopyranoside

Chemical Property of p-methylphenyl 3,6-di-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-deoxy-1-thio-α-D-glucopyranoside

Chemical Property:

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Technology Process of p-methylphenyl 3,6-di-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-deoxy-1-thio-α-D-glucopyranoside

There total 7 articles about p-methylphenyl 3,6-di-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-deoxy-1-thio-α-D-glucopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-1-thio-D-glucopyranoside + p-methylphenyl 3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside (1423496-91-6) → p-methylphenyl 3,6-di-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-deoxy-1-thio-α-D-glucopyranoside (1423497-54-4)

Guidance literature:

p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-1-thio-D-glucopyranoside; With silver trifluoromethanesulfonate; p-toluenesulfonyl chloride; In dichloromethane; at -78 ℃; for 0.25h; Inert atmosphere; Molecular sieve;

p-methylphenyl 3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside; In dichloromethane; at -78 ℃; diastereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1002/chem.201203418

Reference yield: 70.0%

p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside (1423496-75-6) + p-methylphenyl 3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside (1423496-91-6) → p-methylphenyl 3,6-di-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-deoxy-1-thio-α-D-glucopyranoside (1423497-54-4)

Guidance literature:

p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside; With silver trifluoromethanesulfonate; In dichloromethane; at -70 ℃; for 1h; Molecular sieve; Inert atmosphere;

With p-methylbenzenesulfenyl chloride; In dichloromethane; at -70 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

p-methylphenyl 3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside; In dichloromethane; at -70 ℃; stereoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1002/anie.202013909

Reference yield:

p-methylphenyl 3,4,6-tri-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside → p-methylphenyl 3,6-di-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-deoxy-1-thio-α-D-glucopyranoside (1423497-54-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: silver trifluoromethanesulfonate / dichloromethane / 1 h / -70 °C / Molecular sieve; Inert atmosphere

2.2: 0.5 h / -70 °C / Molecular sieve; Inert atmosphere

2.3: -70 °C / Molecular sieve; Inert atmosphere

With silver trifluoromethanesulfonate; sodium hydride; In dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1002/anie.202013909

upstream raw materials:

p-methylphenyl 3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

benzyl bromide

benzaldehyde dimethyl acetal

p-methylphenyl 4,6-O-benzylidene-2-deoxy-1-thio-α-D-glucopyranoside

Downstream raw materials:

methyl 2,3,6-tri-O-benzyl-4-O-(3,6-di-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-deoxy-α-D-glucopyranosyl)-α-D-glucopyranoside

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