[(1R,2R,5R,6R)-6-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-cyclohex-3-enyl]-acetic acid ethyl ester

Base Information

Chemical Name:[(1R,2R,5R,6R)-6-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-cyclohex-3-enyl]-acetic acid ethyl ester
CAS No.:864155-62-4
Molecular Formula:C₁₉H₃₄O₄Si
Molecular Weight:354.562
Hs Code.:

Synonyms:[(1R,2R,5R,6R)-6-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-cyclohex-3-enyl]-acetic acid ethyl ester

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Chemical Property of [(1R,2R,5R,6R)-6-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-cyclohex-3-enyl]-acetic acid ethyl ester

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Technology Process of [(1R,2R,5R,6R)-6-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-cyclohex-3-enyl]-acetic acid ethyl ester

There total 10 articles about [(1R,2R,5R,6R)-6-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-cyclohex-3-enyl]-acetic 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:

: 864155-61-3
[(1R,5R,6R)-6-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-3-enyl]-acetic acid ethyl ester

: 864155-62-4
[(1R,2R,5R,6R)-6-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-cyclohex-3-enyl]-acetic acid ethyl ester

: 864155-63-5
[(1R,2S,5R,6R)-6-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-cyclohex-3-enyl]-acetic acid ethyl ester

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In methanol; at -50 ℃; for 0.25h;
DOI:10.1039/b505264e

Reference yield:

: 864155-60-2
(1S,4R,4aS,7R,8S,8aR)-7-Allyl-8-(tert-butyl-dimethyl-silanyloxy)-4,4a,6,7,8,8a-hexahydro-1H-1,4-methano-naphthalen-5-one

: 864155-62-4
[(1R,2R,5R,6R)-6-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-cyclohex-3-enyl]-acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 85 percent / diphenyl ether / 0.25 h / 210 °C

2: 69 percent / LDA; HMPA / tetrahydrofuran / -78 °C

3: NaBH₄; CeCl₃ / methanol / 0.25 h / -50 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; cerium(III) chloride; diphenylether; lithium diisopropyl amide; In tetrahydrofuran; methanol; 1: retro-Diels-Alder / 3: Luche reduction;
DOI:10.1039/b505264e

Reference yield:

: 864155-59-9
(1S,4R,4aS,5R,8S,8aR)-5-Allyl-8-(tert-butyl-dimethyl-silanyloxy)-1,4,4a,5,8,8a-hexahydro-1,4-methano-naphthalen-5-ol

: 864155-62-4
[(1R,2R,5R,6R)-6-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-cyclohex-3-enyl]-acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 81 percent / KH / dioxane / 0.5 h / 85 °C

2: 85 percent / diphenyl ether / 0.25 h / 210 °C

3: 69 percent / LDA; HMPA / tetrahydrofuran / -78 °C

4: NaBH₄; CeCl₃ / methanol / 0.25 h / -50 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; cerium(III) chloride; diphenylether; potassium hydride; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; 1: oxy-Cope rearrangement / 2: retro-Diels-Alder / 4: Luche reduction;
DOI:10.1039/b505264e