p-tolyl 2-O-(2,2-dimethyl-4-azidobutanoyl)-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:p-tolyl 2-O-(2,2-dimethyl-4-azidobutanoyl)-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside
CAS No.:1431139-38-6
Molecular Formula:C₄₀H₄₅N₃O₆S
Molecular Weight:695.88
Hs Code.:

Synonyms:p-tolyl 2-O-(2,2-dimethyl-4-azidobutanoyl)-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

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Chemical Property of p-tolyl 2-O-(2,2-dimethyl-4-azidobutanoyl)-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

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Technology Process of p-tolyl 2-O-(2,2-dimethyl-4-azidobutanoyl)-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

There total 4 articles about p-tolyl 2-O-(2,2-dimethyl-4-azidobutanoyl)-3,4,6-tri-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:

: 1431139-37-5
2,2-dimethyl-4-azidobutanoyl chloride

: 793672-55-6
p-methylphenyl 3,4,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside

: 1431139-38-6
p-tolyl 2-O-(2,2-dimethyl-4-azidobutanoyl)-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

Guidance literature:: p-methylphenyl 3,4,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside; With 1H-imidazole; sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.5h; Inert atmosphere;

2,2-dimethyl-4-azidobutanoyl chloride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1021/ol4008475

Reference yield:

: 53840-29-2
ethyl 2,2-dimethyl-4-chlorobutanoate

: 1431139-38-6
p-tolyl 2-O-(2,2-dimethyl-4-azidobutanoyl)-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium azide / dimethyl sulfoxide / 14 h / 20 - 70 °C

2.1: lithium hydroxide / ethanol; water / 3 h / Reflux

3.1: oxalyl dichloride / dichloromethane / 1 h / Reflux; Inert atmosphere

4.1: 1H-imidazole; sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

4.2: 0 - 20 °C / Inert atmosphere

With 1H-imidazole; sodium azide; oxalyl dichloride; sodium hydride; lithium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; mineral oil;
DOI:10.1021/ol4008475

Reference yield:

: 1431139-36-4
ethyl 4-azido-2,2-dimethylbutanoate

: 1431139-38-6
p-tolyl 2-O-(2,2-dimethyl-4-azidobutanoyl)-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium hydroxide / ethanol; water / 3 h / Reflux

2.1: oxalyl dichloride / dichloromethane / 1 h / Reflux; Inert atmosphere

3.1: 1H-imidazole; sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

3.2: 0 - 20 °C / Inert atmosphere

With 1H-imidazole; oxalyl dichloride; sodium hydride; lithium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; mineral oil;
DOI:10.1021/ol4008475