p-methylphenyl 2-azido-6-O-acetyl-2-deoxy-3-O-benzyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: p-methylphenyl 2-azido-6-O-acetyl-2-deoxy-3-O-benzyl-1-thio-β-D-glucopyranoside
• CAS No.: 959153-43-6
• Molecular Formula: C₂₂H₂₅N₃O₅S
• Molecular Weight: 443.524

Synonyms:p-methylphenyl 2-azido-6-O-acetyl-2-deoxy-3-O-benzyl-1-thio-β-D-glucopyranoside

Chemical Property of p-methylphenyl 2-azido-6-O-acetyl-2-deoxy-3-O-benzyl-1-thio-β-D-glucopyranoside

Chemical Property:

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Technology Process of p-methylphenyl 2-azido-6-O-acetyl-2-deoxy-3-O-benzyl-1-thio-β-D-glucopyranoside

There total 1 articles about p-methylphenyl 2-azido-6-O-acetyl-2-deoxy-3-O-benzyl-1-thio-β-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: 89.0%

p-tolyl 2-azido-3-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside + acetyl chloride (75-36-5) → p-methylphenyl 2-azido-6-O-acetyl-2-deoxy-3-O-benzyl-1-thio-β-D-glucopyranoside (959153-43-6)

Guidance literature:

With pyridine; at 0 ℃; for 4h;

DOI:10.1021/ja073098r

Reference yield: 92.0%

p-methylphenyl 2-azido-6-O-acetyl-2-deoxy-3-O-benzyl-1-thio-β-D-glucopyranoside (959153-43-6) + p-methylphenyl 2-O-benzoyl-3-O-benzyl-6-O-tert-butyldiphenylsilyl-4-O-levulinyl-1-thio-L-idopyranoside → p-methylphenyl 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-1-thio-4-O-(2-O-benzoyl-3-O-benzyl-6-O-tert-butyldiphenylsilyl-4-O-levulinyl-L-idopyranosyl)-β-D-glucopyranoside

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In diethyl ether; dichloromethane; at -45 - 20 ℃; for 3h;

DOI:10.1021/ja073098r

Reference yield: 90.0%

p-methylphenyl 2-azido-6-O-acetyl-2-deoxy-3-O-benzyl-1-thio-β-D-glucopyranoside (959153-43-6) + t-butyldimethylsiyl triflate (69739-34-0) → p-tolyl 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-1-thio-β-D-glucopyranoside (1242437-13-3)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -40 - 20 ℃; for 5h; Inert atmosphere;

DOI:10.1002/chem.201000987

upstream raw materials:

acetyl chloride

Downstream raw materials:

p-tolyl 2-O-benzoyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-6-O-p-methoxybenzyl-β-D-glucopyranosyl-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside

p-tolyl 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-1-thio-β-D-glucopyranoside

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