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

Base Information

Chemical Name:2-(trimethylsilyl)ethyl 2-O-benzyl-6-O-tert-butyldimethysilyl-4-C-methyl-β-D-glucopyranoside
CAS No.:917568-53-7
Molecular Formula:C₂₅H₄₆O₆Si₂
Molecular Weight:498.808
Hs Code.:

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

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Chemical Property of 2-(trimethylsilyl)ethyl 2-O-benzyl-6-O-tert-butyldimethysilyl-4-C-methyl-β-D-glucopyranoside

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Technology Process of 2-(trimethylsilyl)ethyl 2-O-benzyl-6-O-tert-butyldimethysilyl-4-C-methyl-β-D-glucopyranoside

There total 8 articles about 2-(trimethylsilyl)ethyl 2-O-benzyl-6-O-tert-butyldimethysilyl-4-C-methyl-β-D-glucopyranoside 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: 78.0%

: 917568-52-6
2-(trimethylsilyl)ethyl 2-O-benzyl-6-O-tert-butyldimethysilyl-3-O-p-methoxybenzyl-4-C-methyl-β-D-glucopyranoside

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

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 ℃; 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

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

Guidance literature:: Multi-step reaction with 6 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

With 1H-imidazole; acetic anhydride; sodium hydride; toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/ja065907x

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 4 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

With 1H-imidazole; acetic anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/ja065907x