(2S,4aS,5R,8aR)-2-Bromomethyl-7-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxymethoxy-4,4a,5,8-tetrahydro-benzo[1,3]dioxine-8a-carboxylic acid ethyl ester

Base Information

Chemical Name:(2S,4aS,5R,8aR)-2-Bromomethyl-7-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxymethoxy-4,4a,5,8-tetrahydro-benzo[1,3]dioxine-8a-carboxylic acid ethyl ester
CAS No.:136813-82-6
Molecular Formula:C₃₁H₄₁BrO₇Si
Molecular Weight:633.652
Hs Code.:

(2S,4aS,5R,8aR)-2-Bromomethyl-7-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxymethoxy-4,4a,5,8-tetrahydro-benzo[1,3]dioxine-8a-carboxylic acid ethyl ester

Synonyms:(2S,4aS,5R,8aR)-2-Bromomethyl-7-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxymethoxy-4,4a,5,8-tetrahydro-benzo[1,3]dioxine-8a-carboxylic acid ethyl ester

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Chemical Property of (2S,4aS,5R,8aR)-2-Bromomethyl-7-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxymethoxy-4,4a,5,8-tetrahydro-benzo[1,3]dioxine-8a-carboxylic acid ethyl ester

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Technology Process of (2S,4aS,5R,8aR)-2-Bromomethyl-7-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxymethoxy-4,4a,5,8-tetrahydro-benzo[1,3]dioxine-8a-carboxylic acid ethyl ester

There total 12 articles about (2S,4aS,5R,8aR)-2-Bromomethyl-7-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxymethoxy-4,4a,5,8-tetrahydro-benzo[1,3]dioxine-8a-carboxylic acid ethyl 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: 99.0%

: (2S,4aS,5R,8aR)-2-Bromomethyl-7-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4,4a,5,8-tetrahydro-benzo[1,3]dioxine-8a-carboxylic acid ethyl ester

: 107-30-2
chloromethyl methyl ether

: 136813-82-6
(2S,4aS,5R,8aR)-2-Bromomethyl-7-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxymethoxy-4,4a,5,8-tetrahydro-benzo[1,3]dioxine-8a-carboxylic acid ethyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25 ℃; for 18h;
DOI:10.1016/S0040-4039(00)79872-8

Reference yield:

: 136786-24-8
tert-butyl (E,E)-6-hydroxyhexa-2,4-dienoate

: 136813-82-6
(2S,4aS,5R,8aR)-2-Bromomethyl-7-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxymethoxy-4,4a,5,8-tetrahydro-benzo[1,3]dioxine-8a-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 1) Ag(OSO₂CF₃)2, iPr₂NC₂H₅ / PhCH₃, -20 deg C to 25 deg C, 1.5 h

2: BHT / xylene / 70 h / 145 °C

3: MCPBA, NaH₂PO₄ / CH₂Cl₂ / 24 h / 0 deg C to 25 deg C

4: DBU / tetrahydrofuran / 18 h / 25 °C

5: TFA / CH₂Cl₂ / 5 h / 25 °C

6: Et₃N / tetrahydrofuran / 0.5 h / 0 °C

7: NaBH₄ / methanol; tetrahydrofuran / 0.33 h / -40 °C

8: 82 percent / imidazole / dimethylformamide / 22 h / 25 °C

9: 99 percent / iPr₂NC₂H₅ / CH₂Cl₂ / 18 h / 25 °C

With 1H-imidazole; sodium tetrahydroborate; sodium dihydrogenphosphate; 2,6-di-tert-butyl-4-methyl-phenol; Ag(OSO₂CF₃)2; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; xylene;
DOI:10.1016/S0040-4039(00)79872-8

Reference yield:

: 136786-26-0
2-(1,2-Dibromo-ethoxy)-acrylic acid ethyl ester

: 136813-82-6
(2S,4aS,5R,8aR)-2-Bromomethyl-7-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxymethoxy-4,4a,5,8-tetrahydro-benzo[1,3]dioxine-8a-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 1) Ag(OSO₂CF₃)2, iPr₂NC₂H₅ / PhCH₃, -20 deg C to 25 deg C, 1.5 h

2: BHT / xylene / 70 h / 145 °C

3: MCPBA, NaH₂PO₄ / CH₂Cl₂ / 24 h / 0 deg C to 25 deg C

4: DBU / tetrahydrofuran / 18 h / 25 °C

5: TFA / CH₂Cl₂ / 5 h / 25 °C

6: Et₃N / tetrahydrofuran / 0.5 h / 0 °C

7: NaBH₄ / methanol; tetrahydrofuran / 0.33 h / -40 °C

8: 82 percent / imidazole / dimethylformamide / 22 h / 25 °C

9: 99 percent / iPr₂NC₂H₅ / CH₂Cl₂ / 18 h / 25 °C

With 1H-imidazole; sodium tetrahydroborate; sodium dihydrogenphosphate; 2,6-di-tert-butyl-4-methyl-phenol; Ag(OSO₂CF₃)2; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; xylene;
DOI:10.1016/S0040-4039(00)79872-8