O-4-methoxybenzyl-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-6-O-methyl-4-O-acetyl-3-O-(tert-butyldimethylsilyl)-β-D-glucuronate

Base Information

Chemical Name:O-4-methoxybenzyl-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-6-O-methyl-4-O-acetyl-3-O-(tert-butyldimethylsilyl)-β-D-glucuronate
CAS No.:351900-96-4
Molecular Formula:C₅₇H₆₈O₁₅Si
Molecular Weight:1021.24
Hs Code.:

Synonyms:O-4-methoxybenzyl-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-6-O-methyl-4-O-acetyl-3-O-(tert-butyldimethylsilyl)-β-D-glucuronate

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Chemical Property of O-4-methoxybenzyl-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-6-O-methyl-4-O-acetyl-3-O-(tert-butyldimethylsilyl)-β-D-glucuronate

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Technology Process of O-4-methoxybenzyl-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-6-O-methyl-4-O-acetyl-3-O-(tert-butyldimethylsilyl)-β-D-glucuronate

There total 11 articles about O-4-methoxybenzyl-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-6-O-methyl-4-O-acetyl-3-O-(tert-butyldimethylsilyl)-β-D-glucuronate 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: 80.0%

: 351900-92-0
O-4-methoxybenzyl-6-O-methyl-4-O-acetyl-3-O-(tert-butyldimethylsilyl)-β-D-glucuronate

: 3,4,6-tri-O-benzyl-2-O-benzoyl-β-D-galactopyranose

: 351900-96-4
O-4-methoxybenzyl-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-6-O-methyl-4-O-acetyl-3-O-(tert-butyldimethylsilyl)-β-D-glucuronate

Guidance literature:: 3,4,6-tri-O-benzyl-2-O-benzoyl-β-D-galactopyranose; With 2,4,6-tri-tertbutylpyridine; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; In chloroform; at -45 ℃; for 1h;

O-4-methoxybenzyl-6-O-methyl-4-O-acetyl-3-O-(tert-butyldimethylsilyl)-β-D-glucuronate; In chloroform; at 0 ℃; for 1h;

In chloroform; at 23 ℃; for 3.5h; Further stages.;
DOI:10.1021/ol015651u

Reference yield:

: 351900-87-3
methyl 4-O-acetyl-3-O-(tert-butyldimethylsilyl)-glucuronate-D-glycal

: 351900-96-4
O-4-methoxybenzyl-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-6-O-methyl-4-O-acetyl-3-O-(tert-butyldimethylsilyl)-β-D-glucuronate

Guidance literature:: Multi-step reaction with 3 steps

1.1: diphenyl sulfoxide; trifluoromethanesulfonic anhydride; 2,4,6-tri-tert-butylpyridine / CH₂Cl₂ / 1.2 h / -78 - -45 °C

1.2: methanol; triethylamine / CH₂Cl₂ / -45 - 23 °C

2.1: 181 mg / zinc chloride / diethyl ether; CH₂Cl₂ / 10 h / 23 °C

3.1: 314 mg / CHCl₃ / 4 h / -45 - 23 °C

With 2,4,6-tri-tertbutylpyridine; 1,1'-sulfinylbisbenzene; trifluoromethanesulfonic acid anhydride; zinc(II) chloride; In diethyl ether; dichloromethane; chloroform;
DOI:10.1021/ja062364i

Reference yield:

: 351900-86-2
methyl 3-O-(tert-butyldimethylsilyl)-glucuronate-D-glycal

: 351900-96-4
O-4-methoxybenzyl-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-6-O-methyl-4-O-acetyl-3-O-(tert-butyldimethylsilyl)-β-D-glucuronate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 96 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 3.2 h / 23 °C

2.1: diphenyl sulfoxide; trifluoromethanesulfonic anhydride; 2,4,6-tri-tert-butylpyridine / CH₂Cl₂ / 1.2 h / -78 - -45 °C

2.2: methanol; triethylamine / CH₂Cl₂ / -45 - 23 °C

3.1: 181 mg / zinc chloride / diethyl ether; CH₂Cl₂ / 10 h / 23 °C

4.1: 314 mg / CHCl₃ / 4 h / -45 - 23 °C

With dmap; 2,4,6-tri-tertbutylpyridine; 1,1'-sulfinylbisbenzene; trifluoromethanesulfonic acid anhydride; zinc(II) chloride; In diethyl ether; dichloromethane; chloroform;
DOI:10.1021/ja062364i