(1R,2S,5R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-(4-methoxy-benzyloxy)-cyclopent-3-enecarbaldehyde

Base Information

Chemical Name:(1R,2S,5R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-(4-methoxy-benzyloxy)-cyclopent-3-enecarbaldehyde
CAS No.:913617-88-6
Molecular Formula:C₃₂H₃₈O₄Si
Molecular Weight:514.737
Hs Code.:

Synonyms:(1R,2S,5R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-(4-methoxy-benzyloxy)-cyclopent-3-enecarbaldehyde

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Chemical Property of (1R,2S,5R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-(4-methoxy-benzyloxy)-cyclopent-3-enecarbaldehyde

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Technology Process of (1R,2S,5R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-(4-methoxy-benzyloxy)-cyclopent-3-enecarbaldehyde

There total 9 articles about (1R,2S,5R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-(4-methoxy-benzyloxy)-cyclopent-3-enecarbaldehyde 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: 95.0%

: 913617-82-0
[5-[2-(tert-butyldiphenylsilanyloxy)ethyl]-2-(4-methoxybenzyloxy)-3-cyclopentenyl]methanol

: 913617-88-6
(1R,2S,5R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-(4-methoxy-benzyloxy)-cyclopent-3-enecarbaldehyde

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1016/j.tet.2006.08.068

Reference yield:

: 913617-64-8
(4R)-4-vinyltetrahydropyran-2-one

: 913617-88-6
(1R,2S,5R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-(4-methoxy-benzyloxy)-cyclopent-3-enecarbaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1.1: dibutylboron trifluoromethane sulfonate; diisopropylethylamine / CH₂Cl₂ / 2 h / -78 °C

1.2: 80 percent / CH₂Cl₂ / 1 h / -78 °C

2.1: camphorsulfonic acid / CH₂Cl₂; cyclohexane / 24 h / 20 °C

3.1: 839.5 mg / LiAlH₄ / diethyl ether / 2 h / 20 °C

4.1: 78 percent / benzylidene-bis(tricyclohexylphosphine)dichlororuthenium / toluene / 1.5 h / 50 °C

5.1: 53 percent / imidazole / dimethylformamide / 1 h / 0 °C

6.1: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; Grubbs catalyst first generation; In diethyl ether; dichloromethane; cyclohexane; N,N-dimethyl-formamide; toluene; 1.1: Mukaiyama aldol reaction / 1.2: Mukaiyama aldol reaction;
DOI:10.1016/j.tet.2006.08.068

Reference yield:

: (R)-3-(2-Hydroxy-ethyl)-pent-4-enoic acid

: 913617-88-6
(1R,2S,5R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-(4-methoxy-benzyloxy)-cyclopent-3-enecarbaldehyde

Guidance literature:: Multi-step reaction with 7 steps

1.1: 1.54 g / camphorsulfonic acid / benzene / 15 h / Heating

2.1: dibutylboron trifluoromethane sulfonate; diisopropylethylamine / CH₂Cl₂ / 2 h / -78 °C

2.2: 80 percent / CH₂Cl₂ / 1 h / -78 °C

3.1: camphorsulfonic acid / CH₂Cl₂; cyclohexane / 24 h / 20 °C

4.1: 839.5 mg / LiAlH₄ / diethyl ether / 2 h / 20 °C

5.1: 78 percent / benzylidene-bis(tricyclohexylphosphine)dichlororuthenium / toluene / 1.5 h / 50 °C

6.1: 53 percent / imidazole / dimethylformamide / 1 h / 0 °C

7.1: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; Grubbs catalyst first generation; camphor-10-sulfonic acid; In diethyl ether; dichloromethane; cyclohexane; N,N-dimethyl-formamide; toluene; benzene; 2.1: Mukaiyama aldol reaction / 2.2: Mukaiyama aldol reaction;
DOI:10.1016/j.tet.2006.08.068