phenyl {3-O-acetyl-2-deoxy-6-O-p-methoxybenzyl-2-tetrachlorophthalimido-β-D-glucopyranosyl-(1->2)-[2-(trimethylsilyl)ethyl 4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranosid]} uronate

Base Information

Chemical Name:phenyl {3-O-acetyl-2-deoxy-6-O-p-methoxybenzyl-2-tetrachlorophthalimido-β-D-glucopyranosyl-(1->2)-[2-(trimethylsilyl)ethyl 4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranosid]} uronate
CAS No.:917568-62-8
Molecular Formula:C₄₉H₅₁Cl₄NO₁₇Si
Molecular Weight:1095.84
Hs Code.:

phenyl {3-O-acetyl-2-deoxy-6-O-p-methoxybenzyl-2-tetrachlorophthalimido-β-D-glucopyranosyl-(1->2)-[2-(trimethylsilyl)ethyl 4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranosid]} uronate

Synonyms:phenyl {3-O-acetyl-2-deoxy-6-O-p-methoxybenzyl-2-tetrachlorophthalimido-β-D-glucopyranosyl-(1->2)-[2-(trimethylsilyl)ethyl 4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranosid]} uronate

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Chemical Property of phenyl {3-O-acetyl-2-deoxy-6-O-p-methoxybenzyl-2-tetrachlorophthalimido-β-D-glucopyranosyl-(1->2)-[2-(trimethylsilyl)ethyl 4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranosid]} uronate

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Technology Process of phenyl {3-O-acetyl-2-deoxy-6-O-p-methoxybenzyl-2-tetrachlorophthalimido-β-D-glucopyranosyl-(1->2)-[2-(trimethylsilyl)ethyl 4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranosid]} uronate

There total 18 articles about phenyl {3-O-acetyl-2-deoxy-6-O-p-methoxybenzyl-2-tetrachlorophthalimido-β-D-glucopyranosyl-(1->2)-[2-(trimethylsilyl)ethyl 4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranosid]} uronate 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: 83.0%

: phenyl {3-O-acetyl-2-deoxy-4,6-O-p-methoxybenzylidene-2-tetrachlorophthalimido-β-D-grucopyranosyl-(1-2)-[2-(trimethylsilyl)ethyl 4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranosid]}uronate

: 917568-62-8
phenyl {3-O-acetyl-2-deoxy-6-O-p-methoxybenzyl-2-tetrachlorophthalimido-β-D-glucopyranosyl-(1->2)-[2-(trimethylsilyl)ethyl 4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranosid]} uronate

Guidance literature:: phenyl {3-O-acetyl-2-deoxy-4,6-O-p-methoxybenzylidene-2-tetrachlorophthalimido-β-D-grucopyranosyl-(1-2)-[2-(trimethylsilyl)ethyl 4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranosid]}uronate; With borane-THF; In tetrahydrofuran; at -65 ℃; for 0.0833333h;

With di-n-butylboryl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; at -65 ℃; for 6h;

Reference yield: 83.0%

: 917568-61-7
phenyl {3-O-acetyl-2-deoxy-4,6-O-p-methoxybenzylidene-2-tetrachlorophthalimido-β-D-glucopyranosyl-(1->2)-[2-(trimethylsilyl)ethyl 4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranosid]} uronate

: 917568-62-8
phenyl {3-O-acetyl-2-deoxy-6-O-p-methoxybenzyl-2-tetrachlorophthalimido-β-D-glucopyranosyl-(1->2)-[2-(trimethylsilyl)ethyl 4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranosid]} uronate

Guidance literature:: With borane-THF; di-n-butylboryl trifluoromethanesulfonate; In dichloromethane; at -65 ℃; for 6h;
DOI:10.1021/ja065907x

Reference yield:

: 917568-53-7
2-(trimethylsilyl)ethyl 2-O-benzyl-6-O-tert-butyldimethysilyl-4-C-methyl-β-D-glucopyranoside

: 917568-62-8
phenyl {3-O-acetyl-2-deoxy-6-O-p-methoxybenzyl-2-tetrachlorophthalimido-β-D-glucopyranosyl-(1->2)-[2-(trimethylsilyl)ethyl 4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranosid]} uronate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 100 percent / CH₂Cl₂; pyridine / 0.33 h / 0 °C

2.1: 96 percent / p-toluenesulfonic acid monohydrate / acetonitrile; H₂O / 3 h

3.1: potassium dichromate / acetone; aq. H₂SO₄ / 1 h / 70 °C

4.1: 489 mg / 4-dimethylaminopyridine; N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / CH₂Cl₂

5.1: 98 percent / H₂ / Pd/C / tetrahydrofuran / 760 Torr

6.1: 4-allyl-1,2-dimethoxybenzene / CH₂Cl₂ / 1 h / 20 °C

6.2: 84 percent / triflic anhydride; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 1 h / -42 °C

7.1: 83 percent / BH₃*THF; dibutylboron triflate / CH₂Cl₂ / 6 h / -65 °C

With dmap; potassium dichromate; borane-THF; 1,2-dimethoxy-4-(2-propenyl)benzene; di-n-butylboryl trifluoromethanesulfonate; hydrogen; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; pyridine; dichloromethane; sulfuric acid; water; acetone; acetonitrile;
DOI:10.1021/ja065907x