phenyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4-O-benzyl-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:phenyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4-O-benzyl-1-thio-β-D-glucopyranoside
CAS No.:617698-96-1
Molecular Formula:C₃₃H₃₀ClN₃O₆S
Molecular Weight:632.137
Hs Code.:

Synonyms:phenyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4-O-benzyl-1-thio-β-D-glucopyranoside

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Chemical Property of phenyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4-O-benzyl-1-thio-β-D-glucopyranoside

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Technology Process of phenyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4-O-benzyl-1-thio-β-D-glucopyranoside

There total 8 articles about phenyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4-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: 86.0%

: 617698-95-0
phenyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4-O-benzyl-6-O-(triphenylmethyl)-1-thio-β-D-glucopyranoside

: 617698-96-1
phenyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4-O-benzyl-1-thio-β-D-glucopyranoside

Guidance literature:: phenyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4-O-benzyl-6-O-(triphenylmethyl)-1-thio-β-D-glucopyranoside; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃; for 0.5h; Further stages.;
DOI:10.1002/ejoc.200300248

Reference yield:

: 4551-15-9
phenylthiotrimethylsilane

: 617698-96-1
phenyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4-O-benzyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 84 percent / ZnI₂ / CH₂Cl₂ / 20 °C

2.1: 92 percent / sodium methoxide / methanol; tetrahydrofuran / 2 h / 20 °C

3.1: 98 percent / 2,4,6-collidine; tetrabutylammonium perchlorate / CH₂Cl₂ / 2 h / 20 °C

4.1: 94 percent / NaH / dimethylformamide / 2 h / 0 °C

5.1: trifluoroacetic acid / CH₂Cl₂ / 2 h / 20 °C

5.2: 86 percent / NaHCO₃ / tetrahydrofuran; H₂O / 0.5 h / 20 °C

With 2,4,6-trimethyl-pyridine; tetrabutylammonium perchlorate; sodium methylate; sodium hydride; trifluoroacetic acid; zinc(II) iodide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200300248

Reference yield:

: 193887-70-6
4-azido-3-chlorobenzyl bromide

: 617698-96-1
phenyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4-O-benzyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaH / dimethylformamide / 0.25 h / 0 °C

1.2: 98 percent / dimethylformamide / 3 h

2.1: hydrogen chloride / dioxane / 20 °C

2.2: 61 percent / pyridine / 3 h

3.1: 84 percent / ZnI₂ / CH₂Cl₂ / 20 °C

4.1: 92 percent / sodium methoxide / methanol; tetrahydrofuran / 2 h / 20 °C

5.1: 98 percent / 2,4,6-collidine; tetrabutylammonium perchlorate / CH₂Cl₂ / 2 h / 20 °C

6.1: 94 percent / NaH / dimethylformamide / 2 h / 0 °C

7.1: trifluoroacetic acid / CH₂Cl₂ / 2 h / 20 °C

7.2: 86 percent / NaHCO₃ / tetrahydrofuran; H₂O / 0.5 h / 20 °C

With 2,4,6-trimethyl-pyridine; hydrogenchloride; tetrabutylammonium perchlorate; sodium methylate; sodium hydride; trifluoroacetic acid; zinc(II) iodide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200300248