(2E,4R,5R,7R,10Z)-7-(tert-butyldimethylsiloxy)-4-(2-(tert-butyldiphenylsiloxy)ethyl)-11-cyclohexyl-5-(4-methoxybenzyloxy)-4-(triethylsiloxy)undeca-2,10-dien-8-yn-1-ol

Base Information

Chemical Name:(2E,4R,5R,7R,10Z)-7-(tert-butyldimethylsiloxy)-4-(2-(tert-butyldiphenylsiloxy)ethyl)-11-cyclohexyl-5-(4-methoxybenzyloxy)-4-(triethylsiloxy)undeca-2,10-dien-8-yn-1-ol
CAS No.:902782-35-8
Molecular Formula:C₅₅H₈₄O₆Si₃
Molecular Weight:925.525
Hs Code.:

(2E,4R,5R,7R,10Z)-7-(tert-butyldimethylsiloxy)-4-(2-(tert-butyldiphenylsiloxy)ethyl)-11-cyclohexyl-5-(4-methoxybenzyloxy)-4-(triethylsiloxy)undeca-2,10-dien-8-yn-1-ol

Synonyms:(2E,4R,5R,7R,10Z)-7-(tert-butyldimethylsiloxy)-4-(2-(tert-butyldiphenylsiloxy)ethyl)-11-cyclohexyl-5-(4-methoxybenzyloxy)-4-(triethylsiloxy)undeca-2,10-dien-8-yn-1-ol

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Chemical Property of (2E,4R,5R,7R,10Z)-7-(tert-butyldimethylsiloxy)-4-(2-(tert-butyldiphenylsiloxy)ethyl)-11-cyclohexyl-5-(4-methoxybenzyloxy)-4-(triethylsiloxy)undeca-2,10-dien-8-yn-1-ol

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Technology Process of (2E,4R,5R,7R,10Z)-7-(tert-butyldimethylsiloxy)-4-(2-(tert-butyldiphenylsiloxy)ethyl)-11-cyclohexyl-5-(4-methoxybenzyloxy)-4-(triethylsiloxy)undeca-2,10-dien-8-yn-1-ol

There total 15 articles about (2E,4R,5R,7R,10Z)-7-(tert-butyldimethylsiloxy)-4-(2-(tert-butyldiphenylsiloxy)ethyl)-11-cyclohexyl-5-(4-methoxybenzyloxy)-4-(triethylsiloxy)undeca-2,10-dien-8-yn-1-ol 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: 97.0%

: 902782-13-2
ethyl (2E,4R,5R,7R,10Z)-7-(tert-butyldimethylsiloxy)-4-(2-(tert-butyldiphenylsiloxy)ethyl)-11-cyclohexyl-5-(4-methoxybenzyloxy)-4-(triethylsiloxy)undeca-2,10-dien-8-ynoate

: 902782-35-8
(2E,4R,5R,7R,10Z)-7-(tert-butyldimethylsiloxy)-4-(2-(tert-butyldiphenylsiloxy)ethyl)-11-cyclohexyl-5-(4-methoxybenzyloxy)-4-(triethylsiloxy)undeca-2,10-dien-8-yn-1-ol

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at -70 - -60 ℃; for 0.5h;
DOI:10.1002/anie.200600458

Reference yield:

: 902782-30-3
C₁₄H₁₈O₃

: 902782-35-8
(2E,4R,5R,7R,10Z)-7-(tert-butyldimethylsiloxy)-4-(2-(tert-butyldiphenylsiloxy)ethyl)-11-cyclohexyl-5-(4-methoxybenzyloxy)-4-(triethylsiloxy)undeca-2,10-dien-8-yn-1-ol

Guidance literature:: Multi-step reaction with 17 steps

1.1: LiCl; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0.5 h / 0 °C

1.2: 15.7 g / acetonitrile / 1 h / 20 °C

2.1: 96 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 - -60 °C

3.1: 93 percent / tBuOOH; molecular sieves 4 Angstroem; D-(-)-diisopropyl tartrate / Ti(O-iPr)4 / CH₂Cl₂ / 10 h / -20 °C

4.1: 88 percent / PPh₃; CCl₄; NaHCO₃ / 3 h / Heating

5.1: nBuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

6.1: 9.22 g / imidazole / dimethylformamide / 1 h / 20 °C

7.1: O₃; 2,6-lutidine / methanol / 2 h / -78 °C

7.2: Me₂S / methanol / 1 h / 20 °C

8.1: iPr₂NLi / tetrahydrofuran; hexane / 1 h / -78 °C

8.2: tetrahydrofuran; hexane / 0.5 h / -78 °C

9.1: 8.42 g / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

10.1: imidazole / dimethylformamide / 1 h / 20 °C

11.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.5 h

12.1: 7.68 g / tetrahydrofuran / 1 h / -78 °C

13.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

14.1: O₃; 2,6-lutidine / methanol; propan-2-ol / 5 h / -78 °C

14.2: Me₂S / methanol; propan-2-ol / 1 h / 20 °C

15.1: NaH / tetrahydrofuran / 0.33 h / 0 °C

15.2: 7.14 g / tetrahydrofuran / 20 °C

16.1: 87 percent / tBuNH₂; CuI / Pd(PPh₃)4 / benzene / 20 °C

17.1: 97 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 0.5 h / -70 - -60 °C

With 1H-imidazole; 2,6-dimethylpyridine; tert.-butylhydroperoxide; tetrachloromethane; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 4 A molecular sieve; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; tert-butylamine; triethylamine; triphenylphosphine; lithium chloride; lithium diisopropyl amide; titanium(IV) isopropylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile; benzene; 1.2: Horner-Wadsworth-Emmons reaction / 3.1: Sharpless asymmetric epoxidation / 11.1: Swern oxidation / 15.2: Horner-Wadsworth-Emmons reaction / 16.1: Sonogashira reaction;
DOI:10.1002/anie.200600458

Reference yield:

: 902782-31-4
(2E,5R,6E)-5-(4-methoxybenzyloxy)-2,6-octadien-1-ol

: 902782-35-8
(2E,4R,5R,7R,10Z)-7-(tert-butyldimethylsiloxy)-4-(2-(tert-butyldiphenylsiloxy)ethyl)-11-cyclohexyl-5-(4-methoxybenzyloxy)-4-(triethylsiloxy)undeca-2,10-dien-8-yn-1-ol

Guidance literature:: Multi-step reaction with 15 steps

1.1: 93 percent / tBuOOH; molecular sieves 4 Angstroem; D-(-)-diisopropyl tartrate / Ti(O-iPr)4 / CH₂Cl₂ / 10 h / -20 °C

2.1: 88 percent / PPh₃; CCl₄; NaHCO₃ / 3 h / Heating

3.1: nBuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

4.1: 9.22 g / imidazole / dimethylformamide / 1 h / 20 °C

5.1: O₃; 2,6-lutidine / methanol / 2 h / -78 °C

5.2: Me₂S / methanol / 1 h / 20 °C

6.1: iPr₂NLi / tetrahydrofuran; hexane / 1 h / -78 °C

6.2: tetrahydrofuran; hexane / 0.5 h / -78 °C

7.1: 8.42 g / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

8.1: imidazole / dimethylformamide / 1 h / 20 °C

9.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.5 h

10.1: 7.68 g / tetrahydrofuran / 1 h / -78 °C

11.1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

12.1: O₃; 2,6-lutidine / methanol; propan-2-ol / 5 h / -78 °C

12.2: Me₂S / methanol; propan-2-ol / 1 h / 20 °C

13.1: NaH / tetrahydrofuran / 0.33 h / 0 °C

13.2: 7.14 g / tetrahydrofuran / 20 °C

14.1: 87 percent / tBuNH₂; CuI / Pd(PPh₃)4 / benzene / 20 °C

15.1: 97 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 0.5 h / -70 - -60 °C

With 1H-imidazole; 2,6-dimethylpyridine; tert.-butylhydroperoxide; tetrachloromethane; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 4 A molecular sieve; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; ozone; dimethyl sulfoxide; tert-butylamine; triethylamine; triphenylphosphine; lithium diisopropyl amide; titanium(IV) isopropylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; benzene; 1.1: Sharpless asymmetric epoxidation / 9.1: Swern oxidation / 13.2: Horner-Wadsworth-Emmons reaction / 14.1: Sonogashira reaction;
DOI:10.1002/anie.200600458