dimethyl 2-((1S,4R)-4-hydroxy-2-((tert-butyldimethylsilyloxy)methyl)cyclohex-2-enyl)-2-(3-(2-(tert-butyldimethylsilyloxy)ethyl)-1H-indol-2-yl)malonate

Base Information

Chemical Name:dimethyl 2-((1S,4R)-4-hydroxy-2-((tert-butyldimethylsilyloxy)methyl)cyclohex-2-enyl)-2-(3-(2-(tert-butyldimethylsilyloxy)ethyl)-1H-indol-2-yl)malonate
CAS No.:762252-28-8
Molecular Formula:C₃₄H₅₅NO₇Si₂
Molecular Weight:645.984
Hs Code.:

dimethyl 2-((1S,4R)-4-hydroxy-2-((tert-butyldimethylsilyloxy)methyl)cyclohex-2-enyl)-2-(3-(2-(tert-butyldimethylsilyloxy)ethyl)-1H-indol-2-yl)malonate

Synonyms:dimethyl 2-((1S,4R)-4-hydroxy-2-((tert-butyldimethylsilyloxy)methyl)cyclohex-2-enyl)-2-(3-(2-(tert-butyldimethylsilyloxy)ethyl)-1H-indol-2-yl)malonate

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Chemical Property of dimethyl 2-((1S,4R)-4-hydroxy-2-((tert-butyldimethylsilyloxy)methyl)cyclohex-2-enyl)-2-(3-(2-(tert-butyldimethylsilyloxy)ethyl)-1H-indol-2-yl)malonate

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Technology Process of dimethyl 2-((1S,4R)-4-hydroxy-2-((tert-butyldimethylsilyloxy)methyl)cyclohex-2-enyl)-2-(3-(2-(tert-butyldimethylsilyloxy)ethyl)-1H-indol-2-yl)malonate

There total 10 articles about dimethyl 2-((1S,4R)-4-hydroxy-2-((tert-butyldimethylsilyloxy)methyl)cyclohex-2-enyl)-2-(3-(2-(tert-butyldimethylsilyloxy)ethyl)-1H-indol-2-yl)malonate 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: 86.0%

: 762252-24-4
(((1S,6R)-7-oxa-bicyclo[4.1.0]hept-2-en-2-yl)methoxy)(tert-butyl)dimethylsilane

: 762252-23-3
dimethyl 2-(3-(2-(tert-butyldimethylsilyloxy)ethyl)1H-indol-2-yl)malonate

: 762252-28-8
dimethyl 2-((1S,4R)-4-hydroxy-2-((tert-butyldimethylsilyloxy)methyl)cyclohex-2-enyl)-2-(3-(2-(tert-butyldimethylsilyloxy)ethyl)-1H-indol-2-yl)malonate

Guidance literature:: With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; trifuran-2-yl-phosphane; In toluene; at 20 ℃; for 0.333333h;
DOI:10.1021/ja046407b

Reference yield:

: 93-58-3,5705-52-2,80226-58-0
benzoic acid methyl ester

: 762252-28-8
dimethyl 2-((1S,4R)-4-hydroxy-2-((tert-butyldimethylsilyloxy)methyl)cyclohex-2-enyl)-2-(3-(2-(tert-butyldimethylsilyloxy)ethyl)-1H-indol-2-yl)malonate

Guidance literature:: Multi-step reaction with 6 steps

1: 47.8 g / NBS; H₂O / dimethylsulfoxide / 0.17 h / 20 °C

2: 46 percent / lipase AYS "Amano" / 12 h / 40 °C

3: 73 percent / DIBAL / CH₂Cl₂; toluene / 0.08 h / -78 °C

4: NaOMe / methanol / 0.08 h / 20 °C

5: 2.4 g / imidazole / CH₂Cl₂ / 0.08 h / 20 °C

6: 86 percent / Pd₂(dba)3; P(2-furyl)3 / toluene / 0.33 h / 20 °C

With 1H-imidazole; N-Bromosuccinimide; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; trifuran-2-yl-phosphane; lipase AYS "Amano"; water; sodium methylate; diisobutylaluminium hydride; In methanol; dichloromethane; dimethyl sulfoxide; toluene;
DOI:10.1021/ja046407b

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 762252-28-8
dimethyl 2-((1S,4R)-4-hydroxy-2-((tert-butyldimethylsilyloxy)methyl)cyclohex-2-enyl)-2-(3-(2-(tert-butyldimethylsilyloxy)ethyl)-1H-indol-2-yl)malonate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 98 percent / imidazole / CH₂Cl₂ / 0.08 h / 20 °C

2.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

2.2: 71 percent / NaH / tetrahydrofuran / 0 - 20 °C

3.1: 52 percent / Bu₃SnH; Et₃B / toluene; hexane / 0.17 h / 20 °C

4.1: 86 percent / Pd₂(dba)3; P(2-furyl)3 / toluene / 0.33 h / 20 °C

With 1H-imidazole; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; trifuran-2-yl-phosphane; triethyl borane; tri-n-butyl-tin hydride; sodium hydride; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1021/ja046407b