(S)-tert-butyl 3-<(benzyloxycarbonyl)amino>-5-methylhexanoate

Base Information

• Chemical Name: (S)-tert-butyl 3-<(benzyloxycarbonyl)amino>-5-methylhexanoate
• CAS No.: 146398-15-4
• Molecular Formula: C₁₉H₂₉NO₄
• Molecular Weight: 335.444
• Mol file: 146398-15-4.mol

Synonyms:

Chemical Property of (S)-tert-butyl 3-<(benzyloxycarbonyl)amino>-5-methylhexanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-tert-butyl 3-<(benzyloxycarbonyl)amino>-5-methylhexanoate

There total 5 articles about (S)-tert-butyl 3-<(benzyloxycarbonyl)amino>-5-methylhexanoate 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:

(R)-4-hydroxy-2-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester (146398-01-8) → (S)-tert-butyl 3-<(benzyloxycarbonyl)amino>-5-methylhexanoate (146398-15-4)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / -5 °C

2: NaI / acetone / 4 h / Heating

3: tetrahydrofuran / 0.17 h / -50 °C

With pyridine; sodium iodide; In tetrahydrofuran; acetone;

DOI:10.1055/s-1992-26315

Reference yield:

(2R)-2-{[(benzyloxy)carbonyl]amino}-4-tert-butoxy-4-oxobutanoic acid (71449-08-6) → (S)-tert-butyl 3-<(benzyloxycarbonyl)amino>-5-methylhexanoate (146398-15-4)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / tetrahydrofuran / 0.5 h / -10 °C

2: NaBH₄ / tetrahydrofuran; H₂O / 4 h / Ambient temperature

3: pyridine / -5 °C

4: NaI / acetone / 4 h / Heating

5: tetrahydrofuran / 0.17 h / -50 °C

With pyridine; sodium tetrahydroborate; triethylamine; sodium iodide; In tetrahydrofuran; water; acetone;

DOI:10.1055/s-1992-26315

Reference yield:

(R)-3-Benzyloxycarbonylamino-4-ethoxycarbonyloxy-4-oxo-butyric acid tert-butyl ester → (S)-tert-butyl 3-<(benzyloxycarbonyl)amino>-5-methylhexanoate (146398-15-4)

Guidance literature:

Multi-step reaction with 4 steps

1: NaBH₄ / tetrahydrofuran; H₂O / 4 h / Ambient temperature

2: pyridine / -5 °C

3: NaI / acetone / 4 h / Heating

4: tetrahydrofuran / 0.17 h / -50 °C

With pyridine; sodium tetrahydroborate; sodium iodide; In tetrahydrofuran; water; acetone;

DOI:10.1055/s-1992-26315

upstream raw materials:

tert-butyl 3-<(benzyloxycarbonyl)amino>-4-iodobutanoate

(R)-4-hydroxy-2-{[(phenylmethoxy)carbonyl]amino}butanoic acid 1,1-dimethylethyl ester

(2R)-2-{[(benzyloxy)carbonyl]amino}-4-tert-butoxy-4-oxobutanoic acid

tert-butyl 3-<(benzyloxycarbonyl)amino>-4-(O-tosyl)butanoate

Downstream raw materials:

(S)-3-amino-5-methylhexanoic acid

N-Boc-L-β-homoleucine

N-Benzyloxycarbonyl-L-Homoleucine