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

Base Information

Chemical Name:2-(trimethylsilyl)ethyl 2-O-benzyl-4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranuronic acid
CAS No.:917568-56-0
Molecular Formula:C₂₆H₃₄O₉Si
Molecular Weight:518.636
Hs Code.:

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

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Chemical Property of 2-(trimethylsilyl)ethyl 2-O-benzyl-4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranuronic acid

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Technology Process of 2-(trimethylsilyl)ethyl 2-O-benzyl-4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranuronic acid

There total 12 articles about 2-(trimethylsilyl)ethyl 2-O-benzyl-4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranuronic acid 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:

: 917568-55-9
2-(trimethylsilyl)ethyl 2-O-benzyl-4-C-methyl-3-O-phenoxycarbonyl-β-D-glucopyranoside

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

Guidance literature:: With potassium dichromate; In sulfuric acid; acetone; at 70 ℃; for 1h;
DOI:10.1021/ja065907x

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 9 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

With 1H-imidazole; potassium dichromate; acetic anhydride; sodium hydride; toluene-4-sulfonic acid; 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

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

Guidance literature:: Multi-step reaction with 7 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

With 1H-imidazole; potassium dichromate; acetic anhydride; toluene-4-sulfonic acid; 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