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

Base Information

Chemical Name:(3Z,5S)-3-((2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropylidene)-4-[(2S)-pyrrolidinyl]-1,4-pentanediol
CAS No.:251976-87-1
Molecular Formula:C₂₉H₄₃NO₃Si
Molecular Weight:481.751
Hs Code.:

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

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Chemical Property of (3Z,5S)-3-((2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropylidene)-4-[(2S)-pyrrolidinyl]-1,4-pentanediol

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Technology Process of (3Z,5S)-3-((2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropylidene)-4-[(2S)-pyrrolidinyl]-1,4-pentanediol

There total 9 articles about (3Z,5S)-3-((2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropylidene)-4-[(2S)-pyrrolidinyl]-1,4-pentanediol 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: 71.0%

: 444929-05-9
(3Z,5S)-3-((2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropylidene)-5-methyl-5-[(2S)-pyrrolidinyl]dihydro-2(3H)-furanone

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

Guidance literature:: (3Z,5S)-3-((2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropylidene)-5-methyl-5-[(2S)-pyrrolidinyl]dihydro-2(3H)-furanone; With diisobutylaluminium hydride; In toluene; at -30 ℃; for 0.5h;

With potassium carbonate; In water; toluene; at 20 ℃; for 1h; Further stages.;
DOI:10.1021/jo0200466

Reference yield: 66.0%

: 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

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

Guidance literature:: tert-butyl (2S)-2-[(2S,4Z)-4-((2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropylidene)-2-methyl-5-oxotetrahydro-2-furanyl]-1-pyrrolidinecarboxylate; With trifluoroacetic acid;

With diisobutylaluminium hydride;
DOI:10.1016/S0022-328X(02)01160-9

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

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

Guidance literature:: Multi-step reaction with 3 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

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