ethyl (2E,4R,6S,7S,10S,12E)-4-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7-hydroxy-6-(trityloxymethyl)tetradeca-2,12-dienoate

Base Information

Chemical Name:ethyl (2E,4R,6S,7S,10S,12E)-4-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7-hydroxy-6-(trityloxymethyl)tetradeca-2,12-dienoate
CAS No.:866138-88-7
Molecular Formula:C₅₈H₇₆O₆Si₂
Molecular Weight:925.409
Hs Code.:

ethyl (2E,4R,6S,7S,10S,12E)-4-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7-hydroxy-6-(trityloxymethyl)tetradeca-2,12-dienoate

Synonyms:ethyl (2E,4R,6S,7S,10S,12E)-4-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7-hydroxy-6-(trityloxymethyl)tetradeca-2,12-dienoate

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Chemical Property of ethyl (2E,4R,6S,7S,10S,12E)-4-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7-hydroxy-6-(trityloxymethyl)tetradeca-2,12-dienoate

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Technology Process of ethyl (2E,4R,6S,7S,10S,12E)-4-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7-hydroxy-6-(trityloxymethyl)tetradeca-2,12-dienoate

There total 20 articles about ethyl (2E,4R,6S,7S,10S,12E)-4-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7-hydroxy-6-(trityloxymethyl)tetradeca-2,12-dienoate 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:

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

: 866138-88-7
ethyl (2E,4R,6S,7S,10S,12E)-4-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7-hydroxy-6-(trityloxymethyl)tetradeca-2,12-dienoate

Guidance literature:: Multi-step reaction with 11 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 / pyridine / 12 h / 70 °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; 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

: 866138-88-7
ethyl (2E,4R,6S,7S,10S,12E)-4-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7-hydroxy-6-(trityloxymethyl)tetradeca-2,12-dienoate

Guidance literature:: Multi-step reaction with 6 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 / pyridine / 12 h / 70 °C

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

Reference yield:

: (R)-4-hydroxy-5-(4-methoxybenzyloxy)pentanoic acid

: 866138-88-7
ethyl (2E,4R,6S,7S,10S,12E)-4-(tert-butyldimethylsilyloxy)-10-(tert-butyldiphenylsilyloxy)-7-hydroxy-6-(trityloxymethyl)tetradeca-2,12-dienoate

Guidance literature:: Multi-step reaction with 10 steps

1: imidazole / CH₂Cl₂ / 5 h / 20 °C

2: 6.6 g / aq. K₂CO₃ / methanol; tetrahydrofuran / 1 h / 0 °C

3: Et₃N / tetrahydrofuran / 3 h / 0 °C

4: 6.7 g / BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

5: 93 percent / DDQ; H₂O / CH₂Cl₂ / 0 - 20 °C

6: 100 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

7: 90 percent / BuLi / 1,2-dimethoxy-ethane; hexane / 5 h / 20 °C

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

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

10: 100 percent / pyridine / 12 h / 70 °C

With pyridine; 1H-imidazole; lithium borohydride; n-butyllithium; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; water; potassium carbonate; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; dichloromethane; 6: Swern oxidation / 7: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol051200o