(2E,4E)-8-{(1R,2R)-1-tert-Butoxycarbonylamino-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentyl}-2-methyl-octa-2,4-dienoic acid ethyl ester

Base Information

Chemical Name:(2E,4E)-8-{(1R,2R)-1-tert-Butoxycarbonylamino-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentyl}-2-methyl-octa-2,4-dienoic acid ethyl ester
CAS No.:403507-05-1
Molecular Formula:C₄₀H₅₉NO₅Si
Molecular Weight:661.998
Hs Code.:

(2E,4E)-8-{(1R,2R)-1-tert-Butoxycarbonylamino-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentyl}-2-methyl-octa-2,4-dienoic acid ethyl ester

Synonyms:(2E,4E)-8-{(1R,2R)-1-tert-Butoxycarbonylamino-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentyl}-2-methyl-octa-2,4-dienoic acid ethyl ester

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Chemical Property of (2E,4E)-8-{(1R,2R)-1-tert-Butoxycarbonylamino-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentyl}-2-methyl-octa-2,4-dienoic acid ethyl ester

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Technology Process of (2E,4E)-8-{(1R,2R)-1-tert-Butoxycarbonylamino-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentyl}-2-methyl-octa-2,4-dienoic acid ethyl ester

There total 10 articles about (2E,4E)-8-{(1R,2R)-1-tert-Butoxycarbonylamino-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentyl}-2-methyl-octa-2,4-dienoic 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: 75.0%

: 250595-69-8
{1-allyl-2-[2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentyl}-carbamic acid tert-butyl ester

: 403507-04-0
ethyl (2E,4E)-2-methyl-5-iodopenta-2,4-dienoate

: 403507-05-1
(2E,4E)-8-{(1R,2R)-1-tert-Butoxycarbonylamino-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentyl}-2-methyl-octa-2,4-dienoic acid ethyl ester

Guidance literature:: {1-allyl-2-[2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentyl}-carbamic acid tert-butyl ester; With 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; at 25 ℃; for 1.5h;

ethyl (2E,4E)-2-methyl-5-iodopenta-2,4-dienoate; With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; triphenyl-arsane; caesium carbonate; In water; N,N-dimethyl-formamide; at 25 ℃; for 3h;
DOI:10.1002/1521-3773(20011203)40:23<4450::AID-ANIE4450>3.0.CO;2-M

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 403507-05-1
(2E,4E)-8-{(1R,2R)-1-tert-Butoxycarbonylamino-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentyl}-2-methyl-octa-2,4-dienoic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 93 percent / 4-dimethylaminopyridine / tetrahydrofuran / 18 h / 25 °C

2.1: LiHMDS / tetrahydrofuran; hexane / 1 h / -40 °C

3.1: LiOH / tetrahydrofuran; H₂O / 18 h / 25 °C

4.1: ClCO₂Et; Et₃N / tetrahydrofuran / 1 h / -10 °C

4.2: NaBH₄ / methanol / 1 h / 0 - 25 °C

5.1: 96 percent / Et₃N; 4-dimethylaminopyridine / 0 - 25 °C

6.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 1.5 h / 25 °C

6.2: 75 percent / Pd[1,1'-bis(diphenylphosphinyl)ferrocene]Cl₂*CH₂Cl₂; AsPh₃; Cs₂CO₃ / dimethylformamide; H₂O / 3 h / 25 °C

With dmap; lithium hydroxide; chloroformic acid ethyl ester; triethylamine; 9-bora-bicyclo[3.3.1]nonane; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; water; 6.2: Suzuki reaction;
DOI:10.1002/1521-3773(20011203)40:23<4450::AID-ANIE4450>3.0.CO;2-M

Reference yield:

: 161779-70-0
(3R,5aR,8aS)-3-phenyl-hexahydro-1-oxa-3a-aza-cyclopenta[c]pentalen-4-one

: 403507-05-1
(2E,4E)-8-{(1R,2R)-1-tert-Butoxycarbonylamino-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentyl}-2-methyl-octa-2,4-dienoic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 98 percent / TiCl₄ / CH₂Cl₂ / 18 h / -78 - 25 °C

2.1: 88 percent / Na; EtOH / liquid ammonia; tetrahydrofuran / 1 h / -33 °C

3.1: 93 percent / 4-dimethylaminopyridine / tetrahydrofuran / 18 h / 25 °C

4.1: LiHMDS / tetrahydrofuran; hexane / 1 h / -40 °C

5.1: LiOH / tetrahydrofuran; H₂O / 18 h / 25 °C

6.1: ClCO₂Et; Et₃N / tetrahydrofuran / 1 h / -10 °C

6.2: NaBH₄ / methanol / 1 h / 0 - 25 °C

7.1: 96 percent / Et₃N; 4-dimethylaminopyridine / 0 - 25 °C

8.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 1.5 h / 25 °C

8.2: 75 percent / Pd[1,1'-bis(diphenylphosphinyl)ferrocene]Cl₂*CH₂Cl₂; AsPh₃; Cs₂CO₃ / dimethylformamide; H₂O / 3 h / 25 °C

With dmap; lithium hydroxide; ethanol; sodium; chloroformic acid ethyl ester; titanium tetrachloride; triethylamine; 9-bora-bicyclo[3.3.1]nonane; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; ammonia; water; 8.2: Suzuki reaction;
DOI:10.1002/1521-3773(20011203)40:23<4450::AID-ANIE4450>3.0.CO;2-M