4-{[(3-carboxypropanoyl)oxy]methyl}benzyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4,6-di-O-benzyl-β-D-glucopyranoside

Base Information

Chemical Name:4-{[(3-carboxypropanoyl)oxy]methyl}benzyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4,6-di-O-benzyl-β-D-glucopyranoside
CAS No.:617698-88-1
Molecular Formula:C₄₆H₄₄ClN₃O₁₁
Molecular Weight:850.322
Hs Code.:

Synonyms:4-{[(3-carboxypropanoyl)oxy]methyl}benzyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4,6-di-O-benzyl-β-D-glucopyranoside

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Chemical Property of 4-{[(3-carboxypropanoyl)oxy]methyl}benzyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4,6-di-O-benzyl-β-D-glucopyranoside

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Technology Process of 4-{[(3-carboxypropanoyl)oxy]methyl}benzyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4,6-di-O-benzyl-β-D-glucopyranoside

There total 8 articles about 4-{[(3-carboxypropanoyl)oxy]methyl}benzyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4,6-di-O-benzyl-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: 92.0%

: 108-30-5
succinic acid anhydride

: 617698-93-8
4-(hydroxymethyl)benzyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4,6-di-O-benzyl-β-D-glucopyranoside

: 617698-88-1
4-{[(3-carboxypropanoyl)oxy]methyl}benzyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4,6-di-O-benzyl-β-D-glucopyranoside

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1002/ejoc.200300248

Reference yield:

: 100-39-0
benzyl bromide

: 617698-88-1
4-{[(3-carboxypropanoyl)oxy]methyl}benzyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4,6-di-O-benzyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 93 percent / NaH / dimethylformamide / 2 h / 0 °C

2.1: Sn(OTf)2; 4 Angstroem molecular sieves / tetrahydrofuran / 0.25 h / 20 °C

2.2: 75 percent / N-bromosuccinimide / tetrahydrofuran / 0.5 h / 0 °C

3.1: 92 percent / dimethylaminopyridine; triethylamine / CH₂Cl₂ / 2 h / 20 °C

With dmap; tin(II) trifluoromethanesulfonate; 4 A molecular sieve; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200300248

Reference yield:

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

: 617698-88-1
4-{[(3-carboxypropanoyl)oxy]methyl}benzyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4,6-di-O-benzyl-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: 93 percent / NaH / dimethylformamide / 2 h / 0 °C

6.1: Sn(OTf)2; 4 Angstroem molecular sieves / tetrahydrofuran / 0.25 h / 20 °C

6.2: 75 percent / N-bromosuccinimide / tetrahydrofuran / 0.5 h / 0 °C

7.1: 92 percent / dimethylaminopyridine; triethylamine / CH₂Cl₂ / 2 h / 20 °C

With hydrogenchloride; dmap; tin(II) trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; sodium hydride; triethylamine; zinc(II) iodide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200300248