(S,E)-pent-3-en-2-yl (S)-3-(tert-butoxycarbonylamino)-4-phenylbutanoate

Base Information

Chemical Name:(S,E)-pent-3-en-2-yl (S)-3-(tert-butoxycarbonylamino)-4-phenylbutanoate
CAS No.:1401088-84-3
Molecular Formula:C₂₀H₂₉NO₄
Molecular Weight:347.455
Hs Code.:

Synonyms:(S,E)-pent-3-en-2-yl (S)-3-(tert-butoxycarbonylamino)-4-phenylbutanoate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (S,E)-pent-3-en-2-yl (S)-3-(tert-butoxycarbonylamino)-4-phenylbutanoate

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Technology Process of (S,E)-pent-3-en-2-yl (S)-3-(tert-butoxycarbonylamino)-4-phenylbutanoate

There total 1 articles about (S,E)-pent-3-en-2-yl (S)-3-(tert-butoxycarbonylamino)-4-phenylbutanoate 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: 38.0%

: 108-05-4,9003-20-7
vinyl acetate

: 1569-50-2
3-penten-2-ol

: 51871-62-6
(S)-3-tert-butoxycarbonylamino-4-phenylbutanoic acid

: 1401088-84-3
(S,E)-pent-3-en-2-yl (S)-3-(tert-butoxycarbonylamino)-4-phenylbutanoate

: 19248-95-4
(R,E)-pent-3-en-2-yl acetate

Guidance literature:: vinyl acetate; 3-penten-2-ol; at 20 ℃; for 24h; Enzymatic reaction;

(S)-3-tert-butoxycarbonylamino-4-phenylbutanoic acid; With dmap; dicyclohexyl-carbodiimide; In diethyl ether; at 0 - 20 ℃; stereoselective reaction;
DOI:10.1021/jo301693d

Reference yield: 93.0%

: 1401088-84-3
(S,E)-pent-3-en-2-yl (S)-3-(tert-butoxycarbonylamino)-4-phenylbutanoate

: 1401088-89-8
(3R,E)-2-[(S)-1-(tert-butoxycarbonylamino)-2-phenylethyl]-3-methylhex-4-enoic acid

Guidance literature:: (S,E)-pent-3-en-2-yl (S)-3-(tert-butoxycarbonylamino)-4-phenylbutanoate; With n-butyllithium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 1h; Schlenk technique; Inert atmosphere;

With chloro-trimethyl-silane; In tetrahydrofuran; hexane; at -78 - 60 ℃; for 3h; diastereoselective reaction; Schlenk technique; Inert atmosphere;
DOI:10.1021/jo301693d

Reference yield:

: 1401088-84-3
(S,E)-pent-3-en-2-yl (S)-3-(tert-butoxycarbonylamino)-4-phenylbutanoate

: C₂₅H₃₂N₂O₄S

Guidance literature:: Multi-step reaction with 2 steps

1.1: N-ethyl-N,N-diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 20 °C / Schlenk technique; Inert atmosphere

1.2: 3 h / -78 - 60 °C / Schlenk technique; Inert atmosphere

2.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 0 - 20 °C / Darkness

With dmap; n-butyllithium; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; hexane; dichloromethane; 1.2: |Claisen-Ireland Rearrangement;
DOI:10.1021/jo301693d