(2R,3R,4R)-2-[2-(4-carbomethoxyphenyl)ethyl]-3-[(1E)-4-(tert-butyldimethylsiloxy)-5,5-trimethylene-1-octenyl]-4-(tert-butyldimethylsiloxy)-cyclopentan-1-one

Base Information

Chemical Name:(2R,3R,4R)-2-[2-(4-carbomethoxyphenyl)ethyl]-3-[(1E)-4-(tert-butyldimethylsiloxy)-5,5-trimethylene-1-octenyl]-4-(tert-butyldimethylsiloxy)-cyclopentan-1-one
CAS No.:230311-42-9
Molecular Formula:C₃₈H₆₄O₅Si₂
Molecular Weight:657.094
Hs Code.:

(2R,3R,4R)-2-[2-(4-carbomethoxyphenyl)ethyl]-3-[(1E)-4-(tert-butyldimethylsiloxy)-5,5-trimethylene-1-octenyl]-4-(tert-butyldimethylsiloxy)-cyclopentan-1-one

Synonyms:(2R,3R,4R)-2-[2-(4-carbomethoxyphenyl)ethyl]-3-[(1E)-4-(tert-butyldimethylsiloxy)-5,5-trimethylene-1-octenyl]-4-(tert-butyldimethylsiloxy)-cyclopentan-1-one

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Chemical Property of (2R,3R,4R)-2-[2-(4-carbomethoxyphenyl)ethyl]-3-[(1E)-4-(tert-butyldimethylsiloxy)-5,5-trimethylene-1-octenyl]-4-(tert-butyldimethylsiloxy)-cyclopentan-1-one

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Technology Process of (2R,3R,4R)-2-[2-(4-carbomethoxyphenyl)ethyl]-3-[(1E)-4-(tert-butyldimethylsiloxy)-5,5-trimethylene-1-octenyl]-4-(tert-butyldimethylsiloxy)-cyclopentan-1-one

There total 8 articles about (2R,3R,4R)-2-[2-(4-carbomethoxyphenyl)ethyl]-3-[(1E)-4-(tert-butyldimethylsiloxy)-5,5-trimethylene-1-octenyl]-4-(tert-butyldimethylsiloxy)-cyclopentan-1-one 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: 28.0%

: [(4-methoxycarbonylphenyl)methyl]zinc bromide

: 230312-08-0
(3R,4R)-2-methylene-3-[(1E)-4-(tert-butyldimethylsiloxy)-5,5-trimethylene-1-octenyl]-4-(tert-butyldimethylsiloxy)cyclopentan-1-one

: 230311-42-9
(2R,3R,4R)-2-[2-(4-carbomethoxyphenyl)ethyl]-3-[(1E)-4-(tert-butyldimethylsiloxy)-5,5-trimethylene-1-octenyl]-4-(tert-butyldimethylsiloxy)-cyclopentan-1-one

Guidance literature:: [(4-methoxycarbonylphenyl)methyl]zinc bromide; (3R,4R)-2-methylene-3-[(1E)-4-(tert-butyldimethylsiloxy)-5,5-trimethylene-1-octenyl]-4-(tert-butyldimethylsiloxy)cyclopentan-1-one; With chloro-trimethyl-silane; In tetrahydrofuran; at -78 - -20 ℃; for 3h;

With pyridinium p-toluenesulfonate; In methanol; diethyl ether; at 20 ℃; for 1h;
DOI:10.1016/S0968-0896(01)00369-8

Reference yield:

: 3721-95-7
Cyclobutanecarboxylic acid

: 230311-42-9
(2R,3R,4R)-2-[2-(4-carbomethoxyphenyl)ethyl]-3-[(1E)-4-(tert-butyldimethylsiloxy)-5,5-trimethylene-1-octenyl]-4-(tert-butyldimethylsiloxy)-cyclopentan-1-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: lithium diisopropylamide / tetrahydrofuran / 12 h / 20 °C

2.1: 100 percent / LiAlH₄ / diethyl ether / 3.5 h / 20 °C

3.1: 59 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

4.1: Mg; mercuric chloride / diethyl ether / 0.17 h / 0 °C

4.2: 85 percent / diethyl ether / 1 h / 20 °C

5.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 0.17 h / 0 - 20 °C

6.1: Cp₂ZrClH / tetrahydrofuran / 0.5 h / 20 °C

6.2: 86 percent / I₂ / tetrahydrofuran / 0.17 h / 20 °C

7.1: 61 percent / t-BuLi; lithium 2-thienylcyanocuprate / diethyl ether; pentane; tetrahydrofuran / 1 h / -78 - 0 °C

8.1: CuCN*2LiCl; Me₃SiCl / tetrahydrofuran / 3 h / -78 - -20 °C

8.2: 28 percent / pyridinium p-toluenesulfonate / methanol; diethyl ether / 1 h / 20 °C

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; Schwartz's reagent; chloro-trimethyl-silane; oxalyl dichloride; tert.-butyl lithium; magnesium; dimethyl sulfoxide; thien-2-yl(cyano)copper lithium; triethylamine; mercury dichloride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; pentane; 3.1: Swern oxidation;
DOI:10.1016/S0968-0896(01)00369-8

Reference yield:

: 58148-14-4
2,2-trimethylenepentanoic acid

: 230311-42-9
(2R,3R,4R)-2-[2-(4-carbomethoxyphenyl)ethyl]-3-[(1E)-4-(tert-butyldimethylsiloxy)-5,5-trimethylene-1-octenyl]-4-(tert-butyldimethylsiloxy)-cyclopentan-1-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: 100 percent / LiAlH₄ / diethyl ether / 3.5 h / 20 °C

2.1: 59 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

3.1: Mg; mercuric chloride / diethyl ether / 0.17 h / 0 °C

3.2: 85 percent / diethyl ether / 1 h / 20 °C

4.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 0.17 h / 0 - 20 °C

5.1: Cp₂ZrClH / tetrahydrofuran / 0.5 h / 20 °C

5.2: 86 percent / I₂ / tetrahydrofuran / 0.17 h / 20 °C

6.1: 61 percent / t-BuLi; lithium 2-thienylcyanocuprate / diethyl ether; pentane; tetrahydrofuran / 1 h / -78 - 0 °C

7.1: CuCN*2LiCl; Me₃SiCl / tetrahydrofuran / 3 h / -78 - -20 °C

7.2: 28 percent / pyridinium p-toluenesulfonate / methanol; diethyl ether / 1 h / 20 °C

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; Schwartz's reagent; chloro-trimethyl-silane; oxalyl dichloride; tert.-butyl lithium; magnesium; dimethyl sulfoxide; thien-2-yl(cyano)copper lithium; triethylamine; mercury dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; pentane; 2.1: Swern oxidation;
DOI:10.1016/S0968-0896(01)00369-8