(E)-(2S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4,7-dimethyl-oct-3-enoic acid

Base Information

Chemical Name:(E)-(2S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4,7-dimethyl-oct-3-enoic acid
CAS No.:852156-39-9
Molecular Formula:C₂₂H₃₃NO₄
Molecular Weight:375.508
Hs Code.:

Synonyms:(E)-(2S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4,7-dimethyl-oct-3-enoic acid

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Chemical Property of (E)-(2S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4,7-dimethyl-oct-3-enoic acid

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Technology Process of (E)-(2S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4,7-dimethyl-oct-3-enoic acid

There total 2 articles about (E)-(2S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4,7-dimethyl-oct-3-enoic acid 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:

: ((E)-(1S,4S)-4-Formyl-1-isobutyl-2-methyl-5-phenyl-pent-2-enyl)-carbamic acid tert-butyl ester

: 852156-39-9
(E)-(2S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4,7-dimethyl-oct-3-enoic acid

Guidance literature:: With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tetrahydrofuran; at 0 - 20 ℃; for 5h;
DOI:10.1021/ja051002s

Reference yield:

: 852156-49-1
((4S)-benzyl-5-hydroxy-(1S)-isobutyl-2-methylpent-(2E)-enyl)-carbamic acid tert-butyl ester

: 852156-39-9
(E)-(2S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4,7-dimethyl-oct-3-enoic acid

Guidance literature:: Multi-step reaction with 2 steps

1: Dess-Martin periodinane / CH₂Cl₂ / 3.5 h / 0 °C

2: 2-methyl-2-butene; aq. NaClO₂; NaH₂PO₄*H₂O / tetrahydrofuran / 5 h / 0 - 20 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 1: Dess-Martin oxidation;
DOI:10.1021/ja051002s

Reference yield:

: 852156-39-9
(E)-(2S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4,7-dimethyl-oct-3-enoic acid

: H-Pro-Val-Orn(Cbz)-OMe

: 852156-29-7
Boc-Leu-ψ[(E)-C(CH3)=CH]-DPhe-Pro-Val-Orn(Cbz)-OMe

Guidance literature:: With dmap; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In chloroform; at 20 ℃; for 96h;
DOI:10.1021/ja051002s