(2E,12E)-(4R,6R,7S,10S)-4-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-7-methanesulfonyloxy-6-(pyridin-2-ylselanylmethyl)-tetradeca-2,12-dienoic acid ethyl ester

Base Information

Chemical Name:(2E,12E)-(4R,6R,7S,10S)-4-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-7-methanesulfonyloxy-6-(pyridin-2-ylselanylmethyl)-tetradeca-2,12-dienoic acid ethyl ester
CAS No.:866138-98-9
Molecular Formula:C₄₅H₆₇NO₇SSeSi₂
Molecular Weight:901.226
Hs Code.:

(2E,12E)-(4R,6R,7S,10S)-4-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-7-methanesulfonyloxy-6-(pyridin-2-ylselanylmethyl)-tetradeca-2,12-dienoic acid ethyl ester

Synonyms:(2E,12E)-(4R,6R,7S,10S)-4-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-7-methanesulfonyloxy-6-(pyridin-2-ylselanylmethyl)-tetradeca-2,12-dienoic acid ethyl ester

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Chemical Property of (2E,12E)-(4R,6R,7S,10S)-4-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-7-methanesulfonyloxy-6-(pyridin-2-ylselanylmethyl)-tetradeca-2,12-dienoic acid ethyl ester

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Technology Process of (2E,12E)-(4R,6R,7S,10S)-4-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-7-methanesulfonyloxy-6-(pyridin-2-ylselanylmethyl)-tetradeca-2,12-dienoic acid ethyl ester

There total 22 articles about (2E,12E)-(4R,6R,7S,10S)-4-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-7-methanesulfonyloxy-6-(pyridin-2-ylselanylmethyl)-tetradeca-2,12-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: 99.0%

: 866138-97-8
ethyl (2E,4R,6S,7S,10S,12E)-4-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7-hydroxy-6-((2-pyridylselenyl)methyl)tetradeca-2,12-dienoate

: 124-63-0
methanesulfonyl chloride

: 866138-98-9
(2E,12E)-(4R,6R,7S,10S)-4-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-7-methanesulfonyloxy-6-(pyridin-2-ylselanylmethyl)-tetradeca-2,12-dienoic acid ethyl ester

Guidance literature:: With pyridine; at 20 ℃; for 5h;
DOI:10.1021/ol051200o

Reference yield:

: 32780-06-6
(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

: 866138-98-9
(2E,12E)-(4R,6R,7S,10S)-4-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-7-methanesulfonyloxy-6-(pyridin-2-ylselanylmethyl)-tetradeca-2,12-dienoic acid ethyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 95 percent / DIBALH / tetrahydrofuran; hexane / -78 - 20 °C

2: 92 percent / Et₃N; DMAP / CH₂Cl₂ / 5 h / 20 °C

3: 95 percent / NaH / tetrahydrofuran / 2 h / 20 °C

4: 99 percent / Li; CuCN / diethyl ether; tetrahydrofuran / -78 - 0 °C

5: 92 percent / imidazole; DMAP / CH₂Cl₂ / 5 h / 20 °C

6: pyridinium p-toluenesulfonate / ethanol / 8 h / 20 °C

7: 100 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

8: 85 percent / Et₃N; Bu₂BOTf / CH₂Cl₂ / -78 - 0 °C

9: 90 percent / LiBH₄ / methanol; tetrahydrofuran / -20 - 20 °C

10: 100 percent / Me₃P / tetrahydrofuran / 2 h / 20 °C

11: 99 percent / pyridine / 5 h / 20 °C

With pyridine; 1H-imidazole; dmap; lithium borohydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; pyridinium p-toluenesulfonate; lithium; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; trimethylphosphane; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; 8: Swern oxidation;
DOI:10.1021/ol051200o

Reference yield:

: 866138-80-9
(4S,6E)-1-(tert-butyldimethylsilyloxy)oct-6-en-4-ol

: 866138-98-9
(2E,12E)-(4R,6R,7S,10S)-4-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-7-methanesulfonyloxy-6-(pyridin-2-ylselanylmethyl)-tetradeca-2,12-dienoic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 92 percent / imidazole; DMAP / CH₂Cl₂ / 5 h / 20 °C

2: pyridinium p-toluenesulfonate / ethanol / 8 h / 20 °C

3: 100 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

4: 85 percent / Et₃N; Bu₂BOTf / CH₂Cl₂ / -78 - 0 °C

5: 90 percent / LiBH₄ / methanol; tetrahydrofuran / -20 - 20 °C

6: 100 percent / Me₃P / tetrahydrofuran / 2 h / 20 °C

7: 99 percent / pyridine / 5 h / 20 °C

With pyridine; 1H-imidazole; dmap; lithium borohydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; trimethylphosphane; In tetrahydrofuran; methanol; ethanol; dichloromethane; 3: Swern oxidation;
DOI:10.1021/ol051200o