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

Base Information

Chemical Name:tert-butyl (2S)-2-[(2S,4Z)-4-((2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropylidene)-2-methyl-5-oxotetrahydro-2-furanyl]-1-pyrrolidinecarboxylate
CAS No.:251976-86-0
Molecular Formula:C₃₄H₄₇NO₅Si
Molecular Weight:577.836
Hs Code.:

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

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

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

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

There total 7 articles about tert-butyl (2S)-2-[(2S,4Z)-4-((2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropylidene)-2-methyl-5-oxotetrahydro-2-furanyl]-1-pyrrolidinecarboxylate 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: 97.0%

: 201230-82-2
carbon monoxide

: 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

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

Guidance literature:: With palladium diacetate; tributyl-amine; triphenylphosphine; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 100 ℃;
DOI:10.1021/ja991918x

Reference yield:

: 251976-84-8
(S)-2-[(Z)-(1S,5S)-6-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-1,5-dimethyl-3-triphenylstannanyl-hex-3-enyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

: 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

Guidance literature:: Multi-step reaction with 2 steps

1: 83 percent / N-iodosuccinimide / CH₂Cl₂ / 0 °C

2: 97 percent / Pd(OAc)2; PPh₃; Bu₃N / hexamethylphosphoric acid triamide / 100 °C

With palladium diacetate; N-iodo-succinimide; tributyl-amine; triphenylphosphine; In N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; 1: Substitution / 2: cyclization; carbonylation;
DOI:10.1021/ja991918x

Reference yield:

: 226079-85-2
(S)-tert-butyl(4,4-dibromo-2-methylbut-3-en-1-yloxy)diphenylsilane

: 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

Guidance literature:: Multi-step reaction with 7 steps

1.1: BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

1.2: 92 percent / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

2.1: 97 percent / triethylamine / CH₂Cl₂ / -40 - 20 °C

3.1: 84 percent / cooper(I) cyanide / tetrahydrofuran / 0.05 h / -85 °C

4.1: HfCl₄ / CH₂Cl₂ / 2 h / -78 - 0 °C

5.1: 374 mg / K₂CO₃ / H₂O; CH₂Cl₂ / 12 h / 20 °C

6.1: triphenyltin hydride; triethylborane / benzene; hexane / 120 h / 20 °C

6.2: 409 mg / N-iodosuccinimide / CH₂Cl₂ / 0.5 h

7.1: 97 percent / palladium(II) acetate; tributylamine; triphenylphosphine / hexamethylphosphoric acid triamide / 4 h / 100 °C

With n-butyllithium; tributyl-amine; triethyl borane; triphenylstannane; copper(I) cyanide; palladium diacetate; hafnium tetrachloride; potassium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; water; benzene;
DOI:10.1021/jo0200466