(1S,3S,5R,6S)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]hydroxymethyl]-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester

Base Information

Chemical Name:(1S,3S,5R,6S)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]hydroxymethyl]-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester
CAS No.:944282-71-7
Molecular Formula:C₂₃H₃₄O₆Si
Molecular Weight:434.605
Hs Code.:

(1S,3S,5R,6S)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]hydroxymethyl]-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester

Synonyms:(1S,3S,5R,6S)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]hydroxymethyl]-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1S,3S,5R,6S)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]hydroxymethyl]-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (1S,3S,5R,6S)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]hydroxymethyl]-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester

There total 4 articles about (1S,3S,5R,6S)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]hydroxymethyl]-2-oxobicyclo[3.1.0]hexane-6-carboxylic 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: 91.0%

: 97315-18-9
p-methoxy-m-(tert-butyldimethylsilyloxy)-benzaldehyde

: 188885-85-0,134176-18-4
(1S,5R,6S)-2-oxo-bicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester

: 944282-71-7
(1S,3S,5R,6S)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]hydroxymethyl]-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester

Guidance literature:: (1S,5R,6S)-2-oxo-bicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 1h;

p-methoxy-m-(tert-butyldimethylsilyloxy)-benzaldehyde; In tetrahydrofuran; Further stages.;
DOI:10.1002/anie.200700517

Reference yield:

: 944282-70-6
(3aR,3bR,4S,4aS,5aR)-hexahydro-2,2-dimethyl-5-oxocyclopropa[3,4]cyclopenta[1,2-d]-1,3-dioxole-4-carboxylic acid ethyl ester

: 944282-71-7
(1S,3S,5R,6S)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]hydroxymethyl]-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 88 percent / aq. HCl / tetrahydrofuran

2.1: methanesulfonyl chloride; Et₃N

2.2: 57 percent / i-Pr₂NEt; H₂ / Pd/C

3.1: lithium diisopropylamide / tetrahydrofuran / 1 h / -78 °C

3.2: 91 percent / tetrahydrofuran

With hydrogenchloride; methanesulfonyl chloride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran;
DOI:10.1002/anie.200700517

Reference yield:

: 115509-13-2
(3aR,6aR)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one

: 944282-71-7
(1S,3S,5R,6S)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]hydroxymethyl]-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 92 percent / DBU

2.1: 88 percent / aq. HCl / tetrahydrofuran

3.1: methanesulfonyl chloride; Et₃N

3.2: 57 percent / i-Pr₂NEt; H₂ / Pd/C

4.1: lithium diisopropylamide / tetrahydrofuran / 1 h / -78 °C

4.2: 91 percent / tetrahydrofuran

With hydrogenchloride; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; In tetrahydrofuran;
DOI:10.1002/anie.200700517