(1R,5R,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-5-methoxymethoxy-6-vinyloxymethyl-cyclohex-3-enecarboxylic acid ethyl ester

Base Information

Chemical Name:(1R,5R,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-5-methoxymethoxy-6-vinyloxymethyl-cyclohex-3-enecarboxylic acid ethyl ester
CAS No.:136813-83-7
Molecular Formula:C₃₁H₄₂O₇Si
Molecular Weight:554.756
Hs Code.:

(1R,5R,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-5-methoxymethoxy-6-vinyloxymethyl-cyclohex-3-enecarboxylic acid ethyl ester

Synonyms:(1R,5R,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-5-methoxymethoxy-6-vinyloxymethyl-cyclohex-3-enecarboxylic acid ethyl ester

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Chemical Property of (1R,5R,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-5-methoxymethoxy-6-vinyloxymethyl-cyclohex-3-enecarboxylic acid ethyl ester

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Technology Process of (1R,5R,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-5-methoxymethoxy-6-vinyloxymethyl-cyclohex-3-enecarboxylic acid ethyl ester

There total 13 articles about (1R,5R,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-5-methoxymethoxy-6-vinyloxymethyl-cyclohex-3-enecarboxylic 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: 98.0%

: 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

: 136813-83-7
(1R,5R,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-5-methoxymethoxy-6-vinyloxymethyl-cyclohex-3-enecarboxylic acid ethyl ester

Guidance literature:: With silver; sodium hydrogencarbonate; zinc; In methanol; at 60 ℃; for 40h;
DOI:10.1016/S0040-4039(00)79872-8

Reference yield:

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

: 136813-83-7
(1R,5R,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-5-methoxymethoxy-6-vinyloxymethyl-cyclohex-3-enecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 10 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

10: 98 percent / Zn-Ag, NaHCO₃ / methanol / 40 h / 60 °C

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

Reference yield:

: 136786-25-9
2-Vinyloxy-acrylic acid ethyl ester

: 136813-83-7
(1R,5R,6S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-1-hydroxy-5-methoxymethoxy-6-vinyloxymethyl-cyclohex-3-enecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: Br₂ / tetrahydrofuran / 0.17 h / -78 °C

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

3: BHT / xylene / 70 h / 145 °C

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

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

6: TFA / CH₂Cl₂ / 5 h / 25 °C

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

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

9: 82 percent / imidazole / dimethylformamide / 22 h / 25 °C

10: 99 percent / iPr₂NC₂H₅ / CH₂Cl₂ / 18 h / 25 °C

11: 98 percent / Zn-Ag, NaHCO₃ / methanol / 40 h / 60 °C

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