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

Base Information

Chemical Name:phenyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4-O-benzyl-6-O-(triphenylmethyl)-1-thio-β-D-glucopyranoside
CAS No.:617698-95-0
Molecular Formula:C₅₂H₄₄ClN₃O₆S
Molecular Weight:874.457
Hs Code.:

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

There total 8 articles about phenyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4-O-benzyl-6-O-(triphenylmethyl)-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: 94.0%

: 100-39-0
benzyl bromide

: 617698-94-9
phenyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-6-O-(triphenylmethyl)-1-thio-β-D-glucopyranoside

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

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 2h;
DOI:10.1002/ejoc.200300248

Reference yield:

: 4551-15-9
phenylthiotrimethylsilane

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

Guidance literature:: Multi-step reaction with 4 steps

1: 84 percent / ZnI₂ / CH₂Cl₂ / 20 °C

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

3: 98 percent / 2,4,6-collidine; tetrabutylammonium perchlorate / CH₂Cl₂ / 2 h / 20 °C

4: 94 percent / NaH / dimethylformamide / 2 h / 0 °C

With 2,4,6-trimethyl-pyridine; tetrabutylammonium perchlorate; sodium methylate; sodium hydride; 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

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

Guidance literature:: Multi-step reaction with 6 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

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