phenyl [2-(trimethylsilyl)ethyl 2-O-benzyl-4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranosid] uronate

Base Information

Chemical Name:phenyl [2-(trimethylsilyl)ethyl 2-O-benzyl-4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranosid] uronate
CAS No.:917568-57-1
Molecular Formula:C₃₂H₃₈O₉Si
Molecular Weight:594.734
Hs Code.:

Synonyms:phenyl [2-(trimethylsilyl)ethyl 2-O-benzyl-4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranosid] uronate

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Chemical Property of phenyl [2-(trimethylsilyl)ethyl 2-O-benzyl-4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranosid] uronate

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Technology Process of phenyl [2-(trimethylsilyl)ethyl 2-O-benzyl-4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranosid] uronate

There total 13 articles about phenyl [2-(trimethylsilyl)ethyl 2-O-benzyl-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: 77.0%

: 917568-56-0
2-(trimethylsilyl)ethyl 2-O-benzyl-4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranuronic acid

: 108-95-2,27073-41-2
phenol

: 917568-57-1
phenyl [2-(trimethylsilyl)ethyl 2-O-benzyl-4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranosid] uronate

Guidance literature:: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 ℃;

Reference yield:

: 848647-23-4
2-(trimethylsilyl)ethyl 4,6-O-benzylidene-3-O-p-methoxybenzyl-β-D-galactopyranoside

: 917568-57-1
phenyl [2-(trimethylsilyl)ethyl 2-O-benzyl-4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranosid] uronate

Guidance literature:: Multi-step reaction with 10 steps

1: 82 percent / NaH / dimethylformamide / 1.5 h / 0 °C

2: 90 percent / p-toluenesulfonic acid monohydrate / methanol / 2 h

3: 96 percent / imidazole / dimethylformamide / 8 h

4: 100 percent / acetic anhydride / dimethylsulfoxide / 3 h / 65 °C

5: 76 percent / diethyl ether / -78 - 20 °C

6: 78 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 1 h / 0 °C

7: 100 percent / CH₂Cl₂; pyridine / 0.33 h / 0 °C

8: 96 percent / p-toluenesulfonic acid monohydrate / acetonitrile; H₂O / 3 h

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

10: 489 mg / 4-dimethylaminopyridine; N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / CH₂Cl₂

With 1H-imidazole; dmap; potassium dichromate; acetic anhydride; sodium hydride; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In pyridine; methanol; diethyl ether; dichloromethane; sulfuric acid; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1021/ja065907x

Reference yield:

: 917568-49-1
2-(trimethylsilyl)ethyl 2-O-benzyl-3-O-p-methoxybenzyl-β-D-galactopyranoside

: 917568-57-1
phenyl [2-(trimethylsilyl)ethyl 2-O-benzyl-4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranosid] uronate

Guidance literature:: Multi-step reaction with 8 steps

1: 96 percent / imidazole / dimethylformamide / 8 h

2: 100 percent / acetic anhydride / dimethylsulfoxide / 3 h / 65 °C

3: 76 percent / diethyl ether / -78 - 20 °C

4: 78 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 1 h / 0 °C

5: 100 percent / CH₂Cl₂; pyridine / 0.33 h / 0 °C

6: 96 percent / p-toluenesulfonic acid monohydrate / acetonitrile; H₂O / 3 h

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

8: 489 mg / 4-dimethylaminopyridine; N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / CH₂Cl₂

With 1H-imidazole; dmap; potassium dichromate; acetic anhydride; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In pyridine; diethyl ether; dichloromethane; sulfuric acid; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1021/ja065907x