(2E,4E,10E)-(7S,15R)-15-(tert-Butyl-diphenyl-silanyloxy)-7-methoxy-2-methyl-hexadeca-2,4,10-trienoic acid benzyl ester

Base Information

Chemical Name:(2E,4E,10E)-(7S,15R)-15-(tert-Butyl-diphenyl-silanyloxy)-7-methoxy-2-methyl-hexadeca-2,4,10-trienoic acid benzyl ester
CAS No.:189163-42-6
Molecular Formula:C₄₁H₅₄O₄Si
Molecular Weight:638.963
Hs Code.:

Synonyms:(2E,4E,10E)-(7S,15R)-15-(tert-Butyl-diphenyl-silanyloxy)-7-methoxy-2-methyl-hexadeca-2,4,10-trienoic acid benzyl ester

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Chemical Property of (2E,4E,10E)-(7S,15R)-15-(tert-Butyl-diphenyl-silanyloxy)-7-methoxy-2-methyl-hexadeca-2,4,10-trienoic acid benzyl ester

Chemical Property:

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Technology Process of (2E,4E,10E)-(7S,15R)-15-(tert-Butyl-diphenyl-silanyloxy)-7-methoxy-2-methyl-hexadeca-2,4,10-trienoic acid benzyl ester

There total 24 articles about (2E,4E,10E)-(7S,15R)-15-(tert-Butyl-diphenyl-silanyloxy)-7-methoxy-2-methyl-hexadeca-2,4,10-trienoic acid benzyl 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:

: 56718-04-8
(4R)-pentane-1,4-diol

: 189163-42-6
(2E,4E,10E)-(7S,15R)-15-(tert-Butyl-diphenyl-silanyloxy)-7-methoxy-2-methyl-hexadeca-2,4,10-trienoic acid benzyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 83 percent / DMAP, Et₃N / CH₂Cl₂ / 24 h

2: 96 percent / imidazole / dimethylformamide / 17 h

3: 88 percent / PPTS / ethanol / 6 h / 55 °C

4: 77 percent / DMAP / CH₂Cl₂ / Ambient temperature

5: 86 percent / dimethylsulfoxide / 1 h / Ambient temperature

6: 1.) n-BuLi / 1.) THF, room temperature, 1 h, 2.) HMPT, room temperature, 16 h.

7: TBAF / tetrahydrofuran / 16 h / Ambient temperature

8: LiAlH₄ / bis-(2-methoxy-ethyl) ether / 24 h / Heating

9: DMAP, Et₃N / CH₂Cl₂ / 24 h

10: imidazole / dimethylformamide / 17 h

11: PPTS / ethanol / 6 h / 55 °C

12: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) from -78 deg C to room temperature.

13: 1.) NaH / 1.) THF, 0 deg C, 2 h, 2.) THF, from -30 deg C to -15 deg C, 1.5 h.

With 1H-imidazole; dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; diethylene glycol dimethyl ether; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo962217a

Reference yield:

: 4328-94-3
pentane-1,3,5-triol

: 189163-42-6
(2E,4E,10E)-(7S,15R)-15-(tert-Butyl-diphenyl-silanyloxy)-7-methoxy-2-methyl-hexadeca-2,4,10-trienoic acid benzyl ester

Guidance literature:: Multi-step reaction with 14 steps

1: 1.) TsOH, HC(OMe)3, 2.) 1N NaOH / 1.) CH₂Cl₂, room temperature, overnight, 2.) MeOH, room temperature, 12 h.

2: DMAP / CH₂Cl₂

3: SiO₂, 6N HCl / CH₂Cl₂ / Ambient temperature

4: DIEA, DMAP / CH₂Cl₂ / 24 h / Ambient temperature

5: NaH / dimethylformamide / 1.) -5 deg C, 1 h, 2.) to room temperatire, 3 h.

6: NaI / acetone / 16 h / Heating

7: 1.) n-BuLi / 1.) THF, room temperature, 1 h, 2.) HMPT, room temperature, 16 h.

8: TBAF / tetrahydrofuran / 16 h / Ambient temperature

9: LiAlH₄ / bis-(2-methoxy-ethyl) ether / 24 h / Heating

10: DMAP, Et₃N / CH₂Cl₂ / 24 h

11: imidazole / dimethylformamide / 17 h

12: PPTS / ethanol / 6 h / 55 °C

13: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) from -78 deg C to room temperature.

14: 1.) NaH / 1.) THF, 0 deg C, 2 h, 2.) THF, from -30 deg C to -15 deg C, 1.5 h.

With 1H-imidazole; hydrogenchloride; dmap; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; silica gel; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; trimethyl orthoformate; In tetrahydrofuran; ethanol; dichloromethane; diethylene glycol dimethyl ether; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo962217a

Reference yield:

: 31572-04-0
2-hydroxy-2-methylbuten-3-oic acid

: 189163-42-6
(2E,4E,10E)-(7S,15R)-15-(tert-Butyl-diphenyl-silanyloxy)-7-methoxy-2-methyl-hexadeca-2,4,10-trienoic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 53 percent / NaHCO₃ / dimethylformamide / Ambient temperature

2: 673 mg / SOCl₂ / CH₂Cl₂ / Heating

3: 82 percent / 3 h / 120 °C

4: 1.) NaH / 1.) THF, 0 deg C, 2 h, 2.) THF, from -30 deg C to -15 deg C, 1.5 h.

With thionyl chloride; sodium hydride; sodium hydrogencarbonate; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo962217a