(2E,8Z)-(5R,6R)-5-(2-Benzyloxy-ethyl)-10-bromo-6-(tert-butyl-dimethyl-silanyloxy)-2,8-dimethyl-deca-2,8-dienoic acid ethyl ester

Base Information

Chemical Name:(2E,8Z)-(5R,6R)-5-(2-Benzyloxy-ethyl)-10-bromo-6-(tert-butyl-dimethyl-silanyloxy)-2,8-dimethyl-deca-2,8-dienoic acid ethyl ester
CAS No.:561063-85-2
Molecular Formula:C₂₉H₄₇BrO₄Si
Molecular Weight:567.679
Hs Code.:

Synonyms:(2E,8Z)-(5R,6R)-5-(2-Benzyloxy-ethyl)-10-bromo-6-(tert-butyl-dimethyl-silanyloxy)-2,8-dimethyl-deca-2,8-dienoic acid ethyl ester

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Chemical Property of (2E,8Z)-(5R,6R)-5-(2-Benzyloxy-ethyl)-10-bromo-6-(tert-butyl-dimethyl-silanyloxy)-2,8-dimethyl-deca-2,8-dienoic acid ethyl ester

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Technology Process of (2E,8Z)-(5R,6R)-5-(2-Benzyloxy-ethyl)-10-bromo-6-(tert-butyl-dimethyl-silanyloxy)-2,8-dimethyl-deca-2,8-dienoic acid ethyl ester

There total 17 articles about (2E,8Z)-(5R,6R)-5-(2-Benzyloxy-ethyl)-10-bromo-6-(tert-butyl-dimethyl-silanyloxy)-2,8-dimethyl-deca-2,8-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:

: 561063-84-1
(2E,8E)-(5R,6R)-5-(2-Benzyloxy-ethyl)-6-(tert-butyl-dimethyl-silanyloxy)-10-hydroxy-2,8-dimethyl-deca-2,8-dienoic acid ethyl ester

: 561063-85-2
(2E,8Z)-(5R,6R)-5-(2-Benzyloxy-ethyl)-10-bromo-6-(tert-butyl-dimethyl-silanyloxy)-2,8-dimethyl-deca-2,8-dienoic acid ethyl ester

: 561063-76-1
(2E,8E)-(5R,6R)-5-(2-Benzyloxy-ethyl)-10-bromo-6-(tert-butyl-dimethyl-silanyloxy)-2,8-dimethyl-deca-2,8-dienoic acid ethyl ester

Guidance literature:: With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20 ℃;

Reference yield:

: 128355-20-4
(3R,4S)-3-tert-butyloxycarbonylmethyl-4-hydroxy-5-tetrahydropyranyloxypentanoic acid γ-lactone

: 561063-85-2
(2E,8Z)-(5R,6R)-5-(2-Benzyloxy-ethyl)-10-bromo-6-(tert-butyl-dimethyl-silanyloxy)-2,8-dimethyl-deca-2,8-dienoic acid ethyl ester

Guidance literature:: Multi-step reaction with 17 steps

1.1: 87 percent / DIBALH / tetrahydrofuran / -78 °C

2.1: 99 percent / (+/-)-CSA / 50 °C

3.1: Et₃N; DMAP / dimethylformamide / 0 - 20 °C

4.1: LiAlH₄ / diethyl ether / 0 - 20 °C

5.1: NaH / tetrahydrofuran; dimethylformamide / 0 - 20 °C

6.1: TBAF / tetrahydrofuran / 20 °C

7.1: Et₃N / CH₂Cl₂ / 0 °C

8.1: NaI / acetone / Heating

9.1: BuLi / tetrahydrofuran / -78 - 20 °C

9.2: tetrahydrofuran / -78 - 20 °C

10.1: (+/-)-CSA / methanol; H₂O / 60 °C

11.1: 72 percent / diethyl ether / -78 °C

12.1: aq. AcOH / 60 °C

13.1: 1,2-dichloro-ethane / 80 °C

14.1: 68 percent / Et₃N; DMAP / dimethylformamide / 40 °C

15.1: 87 percent / PDC; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

16.1: 81 percent / NaBH₄ / methanol / 0 °C

17.1: CBr₄; Ph₃P / CH₂Cl₂ / 20 °C

With dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; carbon tetrabromide; 4 A molecular sieve; 10-camphorsufonic acid; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; acetic acid; triethylamine; triphenylphosphine; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; 13.1: Wittig reaction;

Reference yield:

: 561063-79-4
[(2S,3R)-5-Hydroxy-2-(tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-3-yl]-acetic acid tert-butyl ester

: 561063-85-2
(2E,8Z)-(5R,6R)-5-(2-Benzyloxy-ethyl)-10-bromo-6-(tert-butyl-dimethyl-silanyloxy)-2,8-dimethyl-deca-2,8-dienoic acid ethyl ester

Guidance literature:: Multi-step reaction with 16 steps

1.1: 99 percent / (+/-)-CSA / 50 °C

2.1: Et₃N; DMAP / dimethylformamide / 0 - 20 °C

3.1: LiAlH₄ / diethyl ether / 0 - 20 °C

4.1: NaH / tetrahydrofuran; dimethylformamide / 0 - 20 °C

5.1: TBAF / tetrahydrofuran / 20 °C

6.1: Et₃N / CH₂Cl₂ / 0 °C

7.1: NaI / acetone / Heating

8.1: BuLi / tetrahydrofuran / -78 - 20 °C

8.2: tetrahydrofuran / -78 - 20 °C

9.1: (+/-)-CSA / methanol; H₂O / 60 °C

10.1: 72 percent / diethyl ether / -78 °C

11.1: aq. AcOH / 60 °C

12.1: 1,2-dichloro-ethane / 80 °C

13.1: 68 percent / Et₃N; DMAP / dimethylformamide / 40 °C

14.1: 87 percent / PDC; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

15.1: 81 percent / NaBH₄ / methanol / 0 °C

16.1: CBr₄; Ph₃P / CH₂Cl₂ / 20 °C

With dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; carbon tetrabromide; 4 A molecular sieve; 10-camphorsufonic acid; tetrabutyl ammonium fluoride; sodium hydride; acetic acid; triethylamine; triphenylphosphine; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; 12.1: Wittig reaction;