(6Z,8S,8aS)-6-((2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropylidene)-8-methyloctahydro-8-indolizinol

Base Information

Chemical Name:(6Z,8S,8aS)-6-((2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropylidene)-8-methyloctahydro-8-indolizinol
CAS No.:251976-88-2
Molecular Formula:C₂₉H₄₁NO₂Si
Molecular Weight:463.736
Hs Code.:

Synonyms:(6Z,8S,8aS)-6-((2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropylidene)-8-methyloctahydro-8-indolizinol

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Chemical Property of (6Z,8S,8aS)-6-((2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropylidene)-8-methyloctahydro-8-indolizinol

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Technology Process of (6Z,8S,8aS)-6-((2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropylidene)-8-methyloctahydro-8-indolizinol

There total 11 articles about (6Z,8S,8aS)-6-((2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropylidene)-8-methyloctahydro-8-indolizinol 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: 85.0%

: 251976-87-1
(3Z,5S)-3-((2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropylidene)-4-[(2S)-pyrrolidinyl]-1,4-pentanediol

: 251976-88-2
(6Z,8S,8aS)-6-((2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropylidene)-8-methyloctahydro-8-indolizinol

Guidance literature:: With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1021/ja991918x

Reference yield:

: 251976-86-0
tert-butyl (2S)-2-[(2S,4Z)-4-((2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropylidene)-2-methyl-5-oxotetrahydro-2-furanyl]-1-pyrrolidinecarboxylate

: 251976-88-2
(6Z,8S,8aS)-6-((2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropylidene)-8-methyloctahydro-8-indolizinol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 93 percent / trifluoroacetic acid / CH₂Cl₂ / 2 h / 20 °C

2.1: diisobutylaluminum hydride / toluene / 0.5 h / -30 °C

2.2: 71 percent / K₂CO₃ / toluene; H₂O / 1 h / 20 °C

3.1: 85 percent / triphenylphosphine; carbon tetrabromide / CH₂Cl₂ / 1 h / 20 °C

With carbon tetrabromide; diisobutylaluminium hydride; triphenylphosphine; trifluoroacetic acid; In dichloromethane; toluene;
DOI:10.1021/jo0200466

Reference yield:

: 251976-85-9
tert-butyl (2S)-2-[(1S,3Z,5S)-6-{[tert-butyl(diphenyl)silyl]oxy}-1-hydroxy-3-iodo-1,5-dimethyl-3-hexynyl]-1-pyrrolidinecarboxylate

: 251976-88-2
(6Z,8S,8aS)-6-((2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropylidene)-8-methyloctahydro-8-indolizinol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 97 percent / palladium(II) acetate; tributylamine; triphenylphosphine / hexamethylphosphoric acid triamide / 4 h / 100 °C

2.1: 93 percent / trifluoroacetic acid / CH₂Cl₂ / 2 h / 20 °C

3.1: diisobutylaluminum hydride / toluene / 0.5 h / -30 °C

3.2: 71 percent / K₂CO₃ / toluene; H₂O / 1 h / 20 °C

4.1: 85 percent / triphenylphosphine; carbon tetrabromide / CH₂Cl₂ / 1 h / 20 °C

With tributyl-amine; carbon tetrabromide; palladium diacetate; diisobutylaluminium hydride; triphenylphosphine; trifluoroacetic acid; In N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; toluene;
DOI:10.1021/jo0200466