(R)-[(1R,2R,3S)-3-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-6-methylene-cyclohexyl]-((S)-2,2,4-trimethyl-cyclohex-3-enyl)-acetic acid

Base Information

Chemical Name:(R)-[(1R,2R,3S)-3-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-6-methylene-cyclohexyl]-((S)-2,2,4-trimethyl-cyclohex-3-enyl)-acetic acid
CAS No.:240407-03-8
Molecular Formula:C₃₃H₅₂O₄Si
Molecular Weight:540.859
Hs Code.:

(R)-[(1R,2R,3S)-3-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-6-methylene-cyclohexyl]-((S)-2,2,4-trimethyl-cyclohex-3-enyl)-acetic acid

Synonyms:(R)-[(1R,2R,3S)-3-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-6-methylene-cyclohexyl]-((S)-2,2,4-trimethyl-cyclohex-3-enyl)-acetic acid

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Chemical Property of (R)-[(1R,2R,3S)-3-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-6-methylene-cyclohexyl]-((S)-2,2,4-trimethyl-cyclohex-3-enyl)-acetic acid

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Technology Process of (R)-[(1R,2R,3S)-3-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-6-methylene-cyclohexyl]-((S)-2,2,4-trimethyl-cyclohex-3-enyl)-acetic acid

There total 4 articles about (R)-[(1R,2R,3S)-3-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-6-methylene-cyclohexyl]-((S)-2,2,4-trimethyl-cyclohex-3-enyl)-acetic acid 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: 57.0%

: 240407-02-7
((S)-2,2,4-Trimethyl-cyclohex-3-enyl)-acetic acid (3R,4S)-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-cyclohex-1-enylmethyl ester

: 240407-03-8
(R)-[(1R,2R,3S)-3-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-6-methylene-cyclohexyl]-((S)-2,2,4-trimethyl-cyclohex-3-enyl)-acetic acid

Guidance literature:: With tert-butyldimethylsilyl chloride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; toluene;
DOI:10.1016/S0040-4039(99)00828-X

Reference yield:

: 188052-34-8
((1R,6S)-6-Benzyloxy-3-chloromethyl-1-methyl-cyclohex-2-enylmethoxy)-tert-butyl-dimethyl-silane

: 240407-03-8
(R)-[(1R,2R,3S)-3-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-6-methylene-cyclohexyl]-((S)-2,2,4-trimethyl-cyclohex-3-enyl)-acetic acid

Guidance literature:: Multi-step reaction with 4 steps

1: DMSO; NaHCO₃ / toluene

2: NaBH₄ / methanol

3: 66 percent / EDCI; DMAP / CH₂Cl₂

4: 57 percent / LDA; Et₃N; TBSCl / tetrahydrofuran; hexamethylphosphoric acid triamide; toluene

With dmap; sodium tetrahydroborate; sodium hydrogencarbonate; tert-butyldimethylsilyl chloride; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; toluene; 1: Kornblum oxidation / 2: Reduction / 3: Esterification / 4: Ireland-Claisen rearrangement;
DOI:10.1016/S0040-4039(99)00828-X

Reference yield:

: (3R,4S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-cyclohex-1-enecarbaldehyde

: 240407-03-8
(R)-[(1R,2R,3S)-3-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-6-methylene-cyclohexyl]-((S)-2,2,4-trimethyl-cyclohex-3-enyl)-acetic acid

Guidance literature:: Multi-step reaction with 3 steps

1: NaBH₄ / methanol

2: 66 percent / EDCI; DMAP / CH₂Cl₂

3: 57 percent / LDA; Et₃N; TBSCl / tetrahydrofuran; hexamethylphosphoric acid triamide; toluene

With dmap; sodium tetrahydroborate; tert-butyldimethylsilyl chloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; toluene; 1: Reduction / 2: Esterification / 3: Ireland-Claisen rearrangement;
DOI:10.1016/S0040-4039(99)00828-X