O-4-methoxybenzyl-6-O-methyl-4-O-acetyl-3-O-(tert-butyldimethylsilyl)-β-D-glucuronate

Base Information

Chemical Name:O-4-methoxybenzyl-6-O-methyl-4-O-acetyl-3-O-(tert-butyldimethylsilyl)-β-D-glucuronate
CAS No.:351900-92-0
Molecular Formula:C₂₃H₃₆O₉Si
Molecular Weight:484.619
Hs Code.:

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

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Chemical Property of O-4-methoxybenzyl-6-O-methyl-4-O-acetyl-3-O-(tert-butyldimethylsilyl)-β-D-glucuronate

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Technology Process of O-4-methoxybenzyl-6-O-methyl-4-O-acetyl-3-O-(tert-butyldimethylsilyl)-β-D-glucuronate

There total 8 articles about O-4-methoxybenzyl-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: 67.0%

: 105-13-5
4-Methoxybenzyl alcohol

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

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

Guidance literature:: methyl 4-O-acetyl-3-O-(tert-butyldimethylsilyl)-glucuronate-D-glycal; With 2,4,6-tri-tertbutylpyridine; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; In dichloromethane; at -78 - -40 ℃;

4-Methoxybenzyl alcohol; With triethylamine; zinc(II) chloride; In methanol; diethyl ether; at 23 ℃; for 10h; Further stages.;
DOI:10.1021/ol015651u

Reference yield:

: 351900-88-4
methyl 1,2-anhydro-4-O-acetyl-3-O-(tert-butyldimethylsilyl)-α-D-glucuronate

: 105-13-5
4-Methoxybenzyl alcohol

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

Guidance literature:: With zinc(II) chloride; In diethyl ether; dichloromethane; at 23 ℃; for 10h;
DOI:10.1021/ja062364i

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 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

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