4-bromo-benzoic acid 6a-(tert-butyl-dimethyl-silanyloxymethyl)-3a-ethyl-5-oxo-hexahydro-furo[3,2-b]furan-3-yl ester

Base Information

Chemical Name:4-bromo-benzoic acid 6a-(tert-butyl-dimethyl-silanyloxymethyl)-3a-ethyl-5-oxo-hexahydro-furo[3,2-b]furan-3-yl ester
CAS No.:477772-16-0
Molecular Formula:C₂₂H₃₁BrO₆Si
Molecular Weight:499.474
Hs Code.:

4-bromo-benzoic acid 6a-(<i>tert</i>-butyl-dimethyl-silanyloxymethyl)-3a-ethyl-5-oxo-hexahydro-furo[3,2-<i>b</i>]furan-3-yl ester

Synonyms:4-bromo-benzoic acid 6a-(tert-butyl-dimethyl-silanyloxymethyl)-3a-ethyl-5-oxo-hexahydro-furo[3,2-b]furan-3-yl ester

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Chemical Property of 4-bromo-benzoic acid 6a-(tert-butyl-dimethyl-silanyloxymethyl)-3a-ethyl-5-oxo-hexahydro-furo[3,2-b]furan-3-yl ester

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Technology Process of 4-bromo-benzoic acid 6a-(tert-butyl-dimethyl-silanyloxymethyl)-3a-ethyl-5-oxo-hexahydro-furo[3,2-b]furan-3-yl ester

There total 6 articles about 4-bromo-benzoic acid 6a-(tert-butyl-dimethyl-silanyloxymethyl)-3a-ethyl-5-oxo-hexahydro-furo[3,2-b]furan-3-yl ester 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: 90.0%

: 586-75-4
4-chlorobenzoyl chloride

: 477772-14-8
3a-(tert-butyl-dimethyl-silanyloxymethyl)-6a-ethyl-6-hydroxy-tetrahydro-furo[3,2-b]furan-2-one

: 477772-16-0
4-bromo-benzoic acid 6a-(tert-butyl-dimethyl-silanyloxymethyl)-3a-ethyl-5-oxo-hexahydro-furo[3,2-b]furan-3-yl ester

Guidance literature:: With pyridine; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1039/b205924j

Reference yield:

: 403665-44-1
(R)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-1-furan-3-yl-propan-1-ol

: 477772-16-0
4-bromo-benzoic acid 6a-(tert-butyl-dimethyl-silanyloxymethyl)-3a-ethyl-5-oxo-hexahydro-furo[3,2-b]furan-3-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 96 percent / imidazole; DMAP / dimethylformamide / 0.5 h / 20 °C

2.1: n-BuLi / tetrahydrofuran / -78 °C

2.2: 80 percent / tetrahydrofuran / 0.08 h / -78 °C

3.1: 76 percent / aq. peracetic acid; NaOAc / CH₂Cl₂ / 48 h / 0 - 20 °C

4.1: 93 percent / aq. acetic acid / 24 h / 20 °C

5.1: Et₃N / toluene / 72 h / Heating

5.2: aq. HCl / 48 h / 20 °C

5.3: 45 percent / imidazole; DMAP / dimethylformamide / 1 h / 0 °C

6.1: 90 percent / pyridine / CH₂Cl₂ / 24 h / 20 °C

With pyridine; 1H-imidazole; peracetic acid; dmap; n-butyllithium; sodium acetate; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 5.1: Michael addition;
DOI:10.1039/b205924j

Reference yield:

: 477772-13-7
4-((1R,2R)-1-Ethyl-1,2,3-trihydroxy-propyl)-5H-furan-2-one

: 477772-16-0
4-bromo-benzoic acid 6a-(tert-butyl-dimethyl-silanyloxymethyl)-3a-ethyl-5-oxo-hexahydro-furo[3,2-b]furan-3-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: Et₃N / toluene / 72 h / Heating

1.2: aq. HCl / 48 h / 20 °C

1.3: 45 percent / imidazole; DMAP / dimethylformamide / 1 h / 0 °C

2.1: 90 percent / pyridine / CH₂Cl₂ / 24 h / 20 °C

With pyridine; triethylamine; In dichloromethane; toluene; 1.1: Michael addition;
DOI:10.1039/b205924j