benzoic acid 4-[2(tert-butyldiphenylsilanyloxy)ethyl]-5-(2-oxoethyl)-2-cyclopentenyl ester

Base Information

Chemical Name:benzoic acid 4-[2(tert-butyldiphenylsilanyloxy)ethyl]-5-(2-oxoethyl)-2-cyclopentenyl ester
CAS No.:913617-70-6
Molecular Formula:C₃₂H₃₆O₄Si
Molecular Weight:512.721
Hs Code.:

Synonyms:benzoic acid 4-[2(tert-butyldiphenylsilanyloxy)ethyl]-5-(2-oxoethyl)-2-cyclopentenyl ester

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Chemical Property of benzoic acid 4-[2(tert-butyldiphenylsilanyloxy)ethyl]-5-(2-oxoethyl)-2-cyclopentenyl ester

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Technology Process of benzoic acid 4-[2(tert-butyldiphenylsilanyloxy)ethyl]-5-(2-oxoethyl)-2-cyclopentenyl ester

There total 11 articles about benzoic acid 4-[2(tert-butyldiphenylsilanyloxy)ethyl]-5-(2-oxoethyl)-2-cyclopentenyl 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: 99.0%

: 913617-95-5
Benzoic acid (4R,5R)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-(3,3-dimethyl-oxiranylmethyl)-cyclopent-2-enyl ester

: 913617-70-6
benzoic acid 4-[2(tert-butyldiphenylsilanyloxy)ethyl]-5-(2-oxoethyl)-2-cyclopentenyl ester

Guidance literature:: With sodium periodate; In tert-butyl alcohol; at 20 ℃; for 2h;
DOI:10.1016/j.tet.2006.08.068

Reference yield:

: 913617-92-2
(4S)-4-vinyltetrahydropyran-2-one

: 913617-70-6
benzoic acid 4-[2(tert-butyldiphenylsilanyloxy)ethyl]-5-(2-oxoethyl)-2-cyclopentenyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C

1.2: 94 percent / 3 h

2.1: 98 percent / DIBAL-H / hexane; tetrahydrofuran / -78 - -20 °C

3.1: 94 percent / tetrahydrofuran / 1 h / 0 °C

4.1: 80 percent / second generation Grubbs catalyst / 1.5 h / 20 °C

5.1: 98 percent / triethylamine; 4-dimethylaminopyridine / dimethylformamide / 1 h / 0 °C

6.1: 78 percent / pyridine; 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

7.1: 80 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / 0 °C

8.1: 99 percent / sodium periodate / 2-methyl-propan-2-ol / 2 h / 20 °C

With pyridine; dmap; sodium periodate; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1016/j.tet.2006.08.068

Reference yield:

: 913617-72-8
(3R,4R)-3-(3-methyl-2-butenyl)-4-vinyltetrahydropyran-2-one

: 913617-70-6
benzoic acid 4-[2(tert-butyldiphenylsilanyloxy)ethyl]-5-(2-oxoethyl)-2-cyclopentenyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 98 percent / DIBAL-H / hexane; tetrahydrofuran / -78 - -20 °C

2: 94 percent / tetrahydrofuran / 1 h / 0 °C

3: 80 percent / second generation Grubbs catalyst / 1.5 h / 20 °C

4: 98 percent / triethylamine; 4-dimethylaminopyridine / dimethylformamide / 1 h / 0 °C

5: 78 percent / pyridine; 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

6: 80 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / 0 °C

7: 99 percent / sodium periodate / 2-methyl-propan-2-ol / 2 h / 20 °C

With pyridine; dmap; sodium periodate; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1016/j.tet.2006.08.068