[1S-(1β,2α,3α)]-2-(4-methoxyphenyl)-3-triisopropylsilyloxymethyl cyclopropane-1-carboxylic acid

Base Information

Chemical Name:[1S-(1β,2α,3α)]-2-(4-methoxyphenyl)-3-triisopropylsilyloxymethyl cyclopropane-1-carboxylic acid
CAS No.:443149-82-4
Molecular Formula:C₂₁H₃₄O₄Si
Molecular Weight:378.584
Hs Code.:

Synonyms:[1S-(1β,2α,3α)]-2-(4-methoxyphenyl)-3-triisopropylsilyloxymethyl cyclopropane-1-carboxylic acid

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Chemical Property of [1S-(1β,2α,3α)]-2-(4-methoxyphenyl)-3-triisopropylsilyloxymethyl cyclopropane-1-carboxylic acid

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Technology Process of [1S-(1β,2α,3α)]-2-(4-methoxyphenyl)-3-triisopropylsilyloxymethyl cyclopropane-1-carboxylic acid

There total 4 articles about [1S-(1β,2α,3α)]-2-(4-methoxyphenyl)-3-triisopropylsilyloxymethyl cyclopropane-1-carboxylic 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:

: 443149-81-3
[1R-(1α,2α,3α)]-2-(4-methoxyphenyl)-3-triisopropylsilyloxymethyl-1-N-methyl-N-methoxy cyclopropanecarboxamide

: 443149-82-4
[1S-(1β,2α,3α)]-2-(4-methoxyphenyl)-3-triisopropylsilyloxymethyl cyclopropane-1-carboxylic acid

Guidance literature:: [1R-(1α,2α,3α)]-2-(4-methoxyphenyl)-3-triisopropylsilyloxymethyl-1-N-methyl-N-methoxy cyclopropanecarboxamide; With potassium tert-butylate; In diethyl ether; at 0 - 20 ℃;

With water; In diethyl ether; at 20 ℃; for 0.25h; Further stages.;
DOI:10.1021/jo0110698

Reference yield:

: 37614-59-8
4-(4-methoxyphenyl)prop-2-yn-1-ol

: 443149-82-4
[1S-(1β,2α,3α)]-2-(4-methoxyphenyl)-3-triisopropylsilyloxymethyl cyclopropane-1-carboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: 84 percent / NaOH; H₂; ethylenediamine / Ni(OAc)2*4H₂O; NaBH₄ / ethanol / 72 h / 760.05 Torr

2.1: N,N-dimethylaniline / CH₂Cl₂ / 0.17 h / 0 °C

2.2: 65 percent / triethylamine / CH₂Cl₂ / 20 °C

3.1: Rh₂[5(S)-MEPY]4 / CH₂Cl₂ / 18 h / Heating

3.2: Me₃Al / hexane; CH₂Cl₂ / 20 °C

3.3: 2,6-lutidine / CH₂Cl₂; H₂O / 2 h / 0 °C

4.1: t-BuOK / diethyl ether / 0 - 20 °C

4.2: H₂O / diethyl ether / 0.25 h / 20 °C

With sodium hydroxide; potassium tert-butylate; hydrogen; N,N-dimethyl-aniline; ethylenediamine; sodium tetrahydroborate; Rh₂[(2S)-5-hydroxypyrrolidine-2-COOMe]4; nickel diacetate; In diethyl ether; ethanol; dichloromethane; 2.2: Corey-Myers reaction / 3.2: Weinreb reaction;
DOI:10.1021/jo0110698

Reference yield:

: 173542-65-9
(Z)-3-(4-methoxyphenyl)prop-2-en-1-ol

: 443149-82-4
[1S-(1β,2α,3α)]-2-(4-methoxyphenyl)-3-triisopropylsilyloxymethyl cyclopropane-1-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: N,N-dimethylaniline / CH₂Cl₂ / 0.17 h / 0 °C

1.2: 65 percent / triethylamine / CH₂Cl₂ / 20 °C

2.1: Rh₂[5(S)-MEPY]4 / CH₂Cl₂ / 18 h / Heating

2.2: Me₃Al / hexane; CH₂Cl₂ / 20 °C

2.3: 2,6-lutidine / CH₂Cl₂; H₂O / 2 h / 0 °C

3.1: t-BuOK / diethyl ether / 0 - 20 °C

3.2: H₂O / diethyl ether / 0.25 h / 20 °C

With potassium tert-butylate; N,N-dimethyl-aniline; Rh₂[(2S)-5-hydroxypyrrolidine-2-COOMe]4; In diethyl ether; dichloromethane; 1.2: Corey-Myers reaction / 2.2: Weinreb reaction;
DOI:10.1021/jo0110698