(5S,6E,8Z,11S)-5-allyl-11-(2-(4-methoxybenzyloxy)ethyl)-2,2,13,13,14,14-hexamethyl-3,3-diphenyl-4,12-dioxa-3,13-disilapentadeca-6,8-diene

Base Information

Chemical Name:(5S,6E,8Z,11S)-5-allyl-11-(2-(4-methoxybenzyloxy)ethyl)-2,2,13,13,14,14-hexamethyl-3,3-diphenyl-4,12-dioxa-3,13-disilapentadeca-6,8-diene
CAS No.:937800-19-6
Molecular Formula:C₄₂H₆₀O₄Si₂
Molecular Weight:685.107
Hs Code.:

Synonyms:(5S,6E,8Z,11S)-5-allyl-11-(2-(4-methoxybenzyloxy)ethyl)-2,2,13,13,14,14-hexamethyl-3,3-diphenyl-4,12-dioxa-3,13-disilapentadeca-6,8-diene

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Chemical Property of (5S,6E,8Z,11S)-5-allyl-11-(2-(4-methoxybenzyloxy)ethyl)-2,2,13,13,14,14-hexamethyl-3,3-diphenyl-4,12-dioxa-3,13-disilapentadeca-6,8-diene

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Technology Process of (5S,6E,8Z,11S)-5-allyl-11-(2-(4-methoxybenzyloxy)ethyl)-2,2,13,13,14,14-hexamethyl-3,3-diphenyl-4,12-dioxa-3,13-disilapentadeca-6,8-diene

There total 12 articles about (5S,6E,8Z,11S)-5-allyl-11-(2-(4-methoxybenzyloxy)ethyl)-2,2,13,13,14,14-hexamethyl-3,3-diphenyl-4,12-dioxa-3,13-disilapentadeca-6,8-diene 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: 96.0%

: (5E,7Z,10S)-10-(tert-butyldimethylsilyloxy)-12-(4-methoxybenzyloxy)dodeca-1,5,7-trien-4-ol

: 58479-61-1
tert-butylchlorodiphenylsilane

: 937800-19-6
(5S,6E,8Z,11S)-5-allyl-11-(2-(4-methoxybenzyloxy)ethyl)-2,2,13,13,14,14-hexamethyl-3,3-diphenyl-4,12-dioxa-3,13-disilapentadeca-6,8-diene

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 16h;
DOI:10.1021/jo0701942

Reference yield:

: 624727-26-0
ethyl 5-[(4-methoxybenzyl)oxy]-3-oxopentanoate

: 937800-19-6
(5S,6E,8Z,11S)-5-allyl-11-(2-(4-methoxybenzyloxy)ethyl)-2,2,13,13,14,14-hexamethyl-3,3-diphenyl-4,12-dioxa-3,13-disilapentadeca-6,8-diene

Guidance literature:: Multi-step reaction with 11 steps

1.1: 86 percent / (R)-BINAP; hydrogen / [RuCl₂(C₆H₆)]2 / dimethylformamide; ethanol / 62 h / 20 °C / 15001.5 Torr

2.1: 93 percent / imidazole / dimethylformamide / 16 h / 20 °C

3.1: diisobutylaluminium hydride / CH₂Cl₂; hexane / -78 - 20 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

4.2: tetrahydrofuran; hexane / -78 - 20 °C

5.1: 8.4 g / K₂CO₃ / methanol / 0 - 20 °C

6.1: propionic acid / 7 h / 110 °C

7.1: 99 mg / Al₂O₃ / toluene / 0.25 h / 100 °C

8.1: 95 percent / DIBAL-H / CH₂Cl₂; hexane / 0.08 h / -78 °C

9.1: 91 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 °C

10.1: 85 percent / AgOTf; (S)-Tol-BINAP / tetrahydrofuran / 20 h / -20 °C

11.1: 96 percent / imidazole / dimethylformamide / 16 h / 20 °C

With 1H-imidazole; aluminum oxide; n-butyllithium; oxalyl dichloride; hydrogen; silver trifluoromethanesulfonate; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; propionic acid; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; triethylamine; dichloro(benzene)ruthenium(II) dimer; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: asymmetric Noyori hydrogenation / 9.1: Swern oxidation;
DOI:10.1021/jo0701942

Reference yield:

: 937800-24-3
C₂₄H₄₂O₄Si₂

: 937800-19-6
(5S,6E,8Z,11S)-5-allyl-11-(2-(4-methoxybenzyloxy)ethyl)-2,2,13,13,14,14-hexamethyl-3,3-diphenyl-4,12-dioxa-3,13-disilapentadeca-6,8-diene

Guidance literature:: Multi-step reaction with 7 steps

1: 8.4 g / K₂CO₃ / methanol / 0 - 20 °C

2: propionic acid / 7 h / 110 °C

3: 99 mg / Al₂O₃ / toluene / 0.25 h / 100 °C

4: 95 percent / DIBAL-H / CH₂Cl₂; hexane / 0.08 h / -78 °C

5: 91 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 °C

6: 85 percent / AgOTf; (S)-Tol-BINAP / tetrahydrofuran / 20 h / -20 °C

7: 96 percent / imidazole / dimethylformamide / 16 h / 20 °C

With 1H-imidazole; aluminum oxide; oxalyl dichloride; silver trifluoromethanesulfonate; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; propionic acid; 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 5: Swern oxidation;
DOI:10.1021/jo0701942