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

Base Information

Chemical Name:p-tolyl 2-azido-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-1-thio-β-D-glucopyranoside
CAS No.:1242437-12-2
Molecular Formula:C₃₃H₄₃N₃O₄SSi
Molecular Weight:605.874
Hs Code.:

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

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

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

There total 1 articles about p-tolyl 2-azido-3,6-di-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: 95.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 502692-42-4
p-tolyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside

: 1242437-12-2
p-tolyl 2-azido-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-1-thio-β-D-glucopyranoside

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -40 - 0 ℃; Inert atmosphere;
DOI:10.1002/chem.201000987

Reference yield: 75.0%

: 929040-60-8
p-tolyl 2-O-benzoyl-3-O-benzyl-6-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside

: 1242437-12-2
p-tolyl 2-azido-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-1-thio-β-D-glucopyranoside

: 1242437-20-2
p-tolyl 2-azido-3,6-di-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

Guidance literature:: p-tolyl 2-azido-3,6-di-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:

: 1242437-12-2
p-tolyl 2-azido-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-1-thio-β-D-glucopyranoside

: 1415218-25-5
p-tolyl 2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1→4)-2-O-benzoyl-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: silver trifluoromethanesulfonate / dichloromethane; diethyl ether / 0.08 h / -78 °C / Inert atmosphere; Molecular sieve

1.2: 0.08 h / -78 °C / Inert atmosphere

1.3: 2 h / -78 - 0 °C / Inert atmosphere

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 20 °C / Inert atmosphere

3.1: pyridine hydrogenfluoride / 0 °C / Inert atmosphere

4.1: 1H-imidazole / dichloromethane / 20 °C / Inert atmosphere

With 1H-imidazole; silver trifluoromethanesulfonate; pyridine hydrogenfluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In diethyl ether; dichloromethane; water;
DOI:10.1002/anie.201205601