((S)-1-Benzyl-2-oxo-tridec-3-ynyl)-carbamic acid tert-butyl ester

Base Information

• Chemical Name: ((S)-1-Benzyl-2-oxo-tridec-3-ynyl)-carbamic acid tert-butyl ester
• CAS No.: 158527-18-5
• Molecular Formula: C₂₅H₃₇NO₃
• Molecular Weight: 399.574
• Mol file: 158527-18-5.mol

Synonyms:((S)-1-Benzyl-2-oxo-tridec-3-ynyl)-carbamic acid tert-butyl ester

Chemical Property of ((S)-1-Benzyl-2-oxo-tridec-3-ynyl)-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((S)-1-Benzyl-2-oxo-tridec-3-ynyl)-carbamic acid tert-butyl ester

There total 2 articles about ((S)-1-Benzyl-2-oxo-tridec-3-ynyl)-carbamic acid tert-butyl ester 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: 87.0%

Boc-Phe-OH N,O-dimethyl hydroxamate (87694-53-9) + undecynyllithium (69765-57-7) → ((S)-1-Benzyl-2-oxo-tridec-3-ynyl)-carbamic acid tert-butyl ester (158527-18-5)

Guidance literature:

In tetrahydrofuran; at -23 ℃; for 1h;

DOI:10.1021/jo00096a007

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → ((S)-1-Benzyl-2-oxo-tridec-3-ynyl)-carbamic acid tert-butyl ester (158527-18-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / DCC

2: 87 percent / tetrahydrofuran / 1 h / -23 °C

With dicyclohexyl-carbodiimide; In tetrahydrofuran;

DOI:10.1021/jo00096a007

Reference yield:

((S)-1-Benzyl-2-oxo-tridec-3-ynyl)-carbamic acid tert-butyl ester (158527-18-5) → (+)-preussin (125356-66-3,119463-16-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Hg(OAc)2, 2.) NaBH₄ / 1.) CH₃NO₂, 2.) MeOH, -10 deg C

2: 63 percent / LiAlH₄ / tetrahydrofuran / 4 h / 67 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; mercury(II) diacetate; In tetrahydrofuran;

DOI:10.1021/jo00096a007

upstream raw materials:

Boc-Phe-OH N,O-dimethyl hydroxamate

undecynyllithium

N-tert-butoxycarbonyl-L-phenylalanine

Downstream raw materials:

tert-butyl (2S,3S,5R)-2-benzyl-3-hydroxy-5-nonylpyrrolidine-1-carboxylate

(S)-2-Benzyl-5-nonyl-3-oxo-2,3-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

(+)-preussin