5,7,3',4'-tetra-O-(tert-butyldimethylsilyl)flav-3-en-3-ol 3-O-glucoside

Base Information

Chemical Name:5,7,3',4'-tetra-O-(tert-butyldimethylsilyl)flav-3-en-3-ol 3-O-glucoside
CAS No.:908855-86-7
Molecular Formula:C₅₃H₈₆O₁₅Si₄
Molecular Weight:1075.6
Hs Code.:

Synonyms:5,7,3',4'-tetra-O-(tert-butyldimethylsilyl)flav-3-en-3-ol 3-O-glucoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 5,7,3',4'-tetra-O-(tert-butyldimethylsilyl)flav-3-en-3-ol 3-O-glucoside

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Technology Process of 5,7,3',4'-tetra-O-(tert-butyldimethylsilyl)flav-3-en-3-ol 3-O-glucoside

There total 6 articles about 5,7,3',4'-tetra-O-(tert-butyldimethylsilyl)flav-3-en-3-ol 3-O-glucoside 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: 82.0%

: 908855-85-6
Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4S)-2-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-chroman-3-yloxy]-tetrahydro-pyran-3-yl ester

: 908855-86-7
5,7,3',4'-tetra-O-(tert-butyldimethylsilyl)flav-3-en-3-ol 3-O-glucoside

Guidance literature:: With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at 80 ℃; for 6.5h;
DOI:10.1021/ol0614976

Reference yield:

: 908855-83-4
Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S)-5,7-bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-chroman-3-yloxy]-tetrahydro-pyran-3-yl ester

: 908855-86-7
5,7,3',4'-tetra-O-(tert-butyldimethylsilyl)flav-3-en-3-ol 3-O-glucoside

Guidance literature:: Multi-step reaction with 4 steps

1: H₂ / Pd(OH)2/C / ethyl acetate; methanol / 2 h / 20 °C / 760 Torr

2: 1.02 g / imidazole; DMAP / dimethylformamide / 3 h / 65 °C

3: 74 percent / DDQ / methanol; H₂O / 3 h / 20 °C

4: 82 percent / i-Pr₂NEt; MsCl / 1,2-dichloro-ethane / 6.5 h / 80 °C

With 1H-imidazole; dmap; hydrogen; methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; In methanol; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1021/ol0614976

Reference yield:

: 20728-73-8
5,7,3',4'-tetra-O-benzyl-(+)-catechin

: 908855-86-7
5,7,3',4'-tetra-O-(tert-butyldimethylsilyl)flav-3-en-3-ol 3-O-glucoside

Guidance literature:: Multi-step reaction with 5 steps

1: 71 percent / TMSOTf / CH₂Cl₂ / 2 h / -40 °C

2: H₂ / Pd(OH)2/C / ethyl acetate; methanol / 2 h / 20 °C / 760 Torr

3: 1.02 g / imidazole; DMAP / dimethylformamide / 3 h / 65 °C

4: 74 percent / DDQ / methanol; H₂O / 3 h / 20 °C

5: 82 percent / i-Pr₂NEt; MsCl / 1,2-dichloro-ethane / 6.5 h / 80 °C

With 1H-imidazole; dmap; trimethylsilyl trifluoromethanesulfonate; hydrogen; methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; In methanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1021/ol0614976