benzyl (E)-(5S)-6,6-dimethyl-5-<(tert-butoxycarbonyl)amino>-4-oxo-2-heptenoate

Base Information

• Chemical Name: benzyl (E)-(5S)-6,6-dimethyl-5-<(tert-butoxycarbonyl)amino>-4-oxo-2-heptenoate
• CAS No.: 176504-91-9
• Molecular Formula: C₂₁H₂₉NO₅
• Molecular Weight: 375.465

Synonyms:benzyl (E)-(5S)-6,6-dimethyl-5-<(tert-butoxycarbonyl)amino>-4-oxo-2-heptenoate

Chemical Property of benzyl (E)-(5S)-6,6-dimethyl-5-<(tert-butoxycarbonyl)amino>-4-oxo-2-heptenoate

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Technology Process of benzyl (E)-(5S)-6,6-dimethyl-5-<(tert-butoxycarbonyl)amino>-4-oxo-2-heptenoate

There total 2 articles about benzyl (E)-(5S)-6,6-dimethyl-5-<(tert-butoxycarbonyl)amino>-4-oxo-2-heptenoate 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: 83.0%

benzylglyoxylate (52709-42-9) + dimethyl <(3S)-4,4-dimethyl-3-<(tert-butoxycarbonyl)amino>-2-oxopentyl>phosphonate (176504-89-5) → benzyl (E)-(5S)-6,6-dimethyl-5-<(tert-butoxycarbonyl)amino>-4-oxo-2-heptenoate (176504-91-9)

Guidance literature:

With triethylamine; In acetonitrile; for 1h; Ambient temperature;

DOI:10.1021/jo951988w

Reference yield:

2-tert-butoxycarbonylamino-3,3-dimethylbutyric acid methyl ester (176504-88-4) → benzyl (E)-(5S)-6,6-dimethyl-5-<(tert-butoxycarbonyl)amino>-4-oxo-2-heptenoate (176504-91-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-BuLi / 1.) THF, -78 deg C, 20 min, 2.) -78 deg C, 1 h; room temperature, 15 min

2: 83 percent / Et₃N / acetonitrile / 1 h / Ambient temperature

With n-butyllithium; triethylamine; In acetonitrile;

DOI:10.1021/jo951988w

Reference yield:

tert-butyl allyl malonate (134209-82-8) + benzyl (E)-(5S)-6,6-dimethyl-5-<(tert-butoxycarbonyl)amino>-4-oxo-2-heptenoate (176504-91-9) → 2-Allyloxycarbonyl-3-((S)-3-tert-butoxycarbonylamino-4,4-dimethyl-2-oxo-pentyl)-succinic acid 4-benzyl ester 1-tert-butyl ester

Guidance literature:

With sodium hydride; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1021/jo951988w

upstream raw materials:

benzylglyoxylate

dimethyl <(3S)-4,4-dimethyl-3-<(tert-butoxycarbonyl)amino>-2-oxopentyl>phosphonate

2-tert-butoxycarbonylamino-3,3-dimethylbutyric acid methyl ester

Downstream raw materials:

(S)-2-Allyloxycarbonyl-3-((S)-3-tert-butoxycarbonylamino-4,4-dimethyl-2-oxo-pentyl)-succinic acid 1-allyl ester 4-benzyl ester

(S)-2-((S)-3-tert-Butoxycarbonylamino-4,4-dimethyl-2-oxo-pentyl)-3-(2,2-dimethyl-propionyl)-succinic acid 4-allyl ester 1-benzyl ester

(S)-2-((S)-3-tert-Butoxycarbonylamino-4,4-dimethyl-2-oxo-pentyl)-succinic acid 1-benzyl ester

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