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

Base Information

Chemical Name:tert-butyl (2S)-2-[(1S,3Z,5S)-6-{[tert-butyl(diphenyl)silyl]oxy}-1-hydroxy-3-iodo-1,5-dimethyl-3-hexynyl]-1-pyrrolidinecarboxylate
CAS No.:251976-85-9
Molecular Formula:C₃₃H₄₈INO₄Si
Molecular Weight:677.738
Hs Code.:

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

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Chemical Property of tert-butyl (2S)-2-[(1S,3Z,5S)-6-{[tert-butyl(diphenyl)silyl]oxy}-1-hydroxy-3-iodo-1,5-dimethyl-3-hexynyl]-1-pyrrolidinecarboxylate

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Technology Process of tert-butyl (2S)-2-[(1S,3Z,5S)-6-{[tert-butyl(diphenyl)silyl]oxy}-1-hydroxy-3-iodo-1,5-dimethyl-3-hexynyl]-1-pyrrolidinecarboxylate

There total 7 articles about tert-butyl (2S)-2-[(1S,3Z,5S)-6-{[tert-butyl(diphenyl)silyl]oxy}-1-hydroxy-3-iodo-1,5-dimethyl-3-hexynyl]-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:

: 251976-83-7
tert-butyl (2S)-2-[(1S,5S)-5-{[tert-butyl(diphenyl)silyl]oxy}-1-hydroxy-1,5-dimethyl-3-hexynyl]-1-pyrrolidinecarboxylate

: 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

Guidance literature:: tert-butyl (2S)-2-[(1S,5S)-5-{[tert-butyl(diphenyl)silyl]oxy}-1-hydroxy-1,5-dimethyl-3-hexynyl]-1-pyrrolidinecarboxylate; With triethyl borane; triphenylstannane; In benzene;

With N-iodo-succinimide; In dichloromethane;
DOI:10.1016/S0022-328X(02)01160-9

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 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

Guidance literature:: Multi-step reaction with 2 steps

1.1: 374 mg / K₂CO₃ / H₂O; CH₂Cl₂ / 12 h / 20 °C

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

2.2: 409 mg / N-iodosuccinimide / CH₂Cl₂ / 0.5 h

With triethyl borane; triphenylstannane; potassium carbonate; In hexane; dichloromethane; water; benzene;
DOI:10.1021/jo0200466

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 6 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

With n-butyllithium; triethyl borane; triphenylstannane; copper(I) cyanide; hafnium tetrachloride; potassium carbonate; triethylamine; In tetrahydrofuran; hexane; dichloromethane; water; benzene;
DOI:10.1021/jo0200466