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

Base Information

• Chemical Name: p-tolyl 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-1-thio-β-D-glucopyranoside
• CAS No.: 1242437-13-3
• Molecular Formula: C₂₈H₃₉N₃O₅SSi
• Molecular Weight: 557.786

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

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

Chemical Property:

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

There total 1 articles about p-tolyl 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-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: 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

Reference yield: 89.0%

p-tolyl 2-O-benzoyl-3-O-benzyl-6-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside (929040-60-8) + p-tolyl 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-1-thio-β-D-glucopyranoside (1242437-13-3) → p-tolyl 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-2-O-benzoyl-3-O-benzyl-6-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside (1242437-19-9)

Guidance literature:

p-tolyl 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-1-thio-β-D-glucopyranoside; With silver trifluoromethanesulfonate; In diethyl ether; dichloromethane; at -78 ℃; for 0.0833333h; Inert atmosphere; Molecular sieve;

With p-methylbenzenesulfenyl chloride; In diethyl ether; dichloromethane; at -78 ℃; for 0.0833333h; Inert atmosphere; Molecular sieve;

p-tolyl 2-O-benzoyl-3-O-benzyl-6-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside; With 2,4,6-tri-tert-butylpyrimidine; In diethyl ether; dichloromethane; at -78 - -20 ℃; for 2h; stereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1002/chem.201000987

Reference yield: 85.0%

p-tolyl 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-1-thio-β-D-glucopyranoside (1242437-13-3) + p-tolyl 2-O-benzoyl-3-O-benzyl-6-O-p-methoxybenzyl-1-thio-α-L-idopyranoside (1242437-11-1) → p-tolyl 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-2-O-benzoyl-3-O-benzyl-6-O-p-methoxybenzyl-1-thio-α-L-idopyranoside (1242437-16-6)

Guidance literature:

p-tolyl 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-1-thio-β-D-glucopyranoside; With silver trifluoromethanesulfonate; In diethyl ether; dichloromethane; at -78 - 20 ℃; for 0.583333h; Inert atmosphere; Molecular sieve;

p-tolyl 2-O-benzoyl-3-O-benzyl-6-O-p-methoxybenzyl-1-thio-α-L-idopyranoside; With p-toluenesulfonyl chloride; In diethyl ether; dichloromethane; at -78 ℃; for 0.0833333h; Inert atmosphere; Molecular sieve;

With 2,4,5-tri-tert-butylpyrimidine; In diethyl ether; dichloromethane; at -78 - 0 ℃; for 2h; Inert atmosphere; Molecular sieve;

DOI:10.1021/acs.joc.5b02172

upstream raw materials:

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

t-butyldimethylsiyl triflate

Downstream raw materials:

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

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

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

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

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