(2S,9S)-2,6-cyclo-6-aza-9-(benzyloxycarbonylamino)-10-methylundecanoic acid methyl ester

Base Information

• Chemical Name: (2S,9S)-2,6-cyclo-6-aza-9-(benzyloxycarbonylamino)-10-methylundecanoic acid methyl ester
• CAS No.: 866395-28-0
• Molecular Formula: C₂₀H₃₀N₂O₄
• Molecular Weight: 362.469
• Mol file: 866395-28-0.mol

Synonyms:(2S,9S)-2,6-cyclo-6-aza-9-(benzyloxycarbonylamino)-10-methylundecanoic acid methyl ester

Chemical Property of (2S,9S)-2,6-cyclo-6-aza-9-(benzyloxycarbonylamino)-10-methylundecanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,9S)-2,6-cyclo-6-aza-9-(benzyloxycarbonylamino)-10-methylundecanoic acid methyl ester

There total 10 articles about (2S,9S)-2,6-cyclo-6-aza-9-(benzyloxycarbonylamino)-10-methylundecanoic acid methyl 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: 71.0%

(S)-1-mesyloxy-N-(benzyloxycarbonyl)-3-amino-4-methylpentane (866395-25-7) + methyl (2S)-pyrrolidine carboxylate (2577-48-2) → (2S,9S)-2,6-cyclo-6-aza-9-(benzyloxycarbonylamino)-10-methylundecanoic acid methyl ester (866395-28-0)

Guidance literature:

With triethylamine; In acetonitrile; at 20 - 50 ℃;

DOI:10.1016/j.tet.2005.07.049

Reference yield:

(S)-N-(benzyloxycarbonyl)-3-amino-4-methylpentan-1-ol (866395-22-4) → (2S,9S)-2,6-cyclo-6-aza-9-(benzyloxycarbonylamino)-10-methylundecanoic acid methyl ester (866395-28-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / Et₃N / CH₂Cl₂ / cooling

2: 71 percent / Et₃N / acetonitrile / 20 - 50 °C

With triethylamine; In dichloromethane; acetonitrile;

DOI:10.1016/j.tet.2005.07.049

Reference yield:

(R)-1-diazo-3-phthalimido-4-methylpentan-2-one (866395-48-4) → (2S,9S)-2,6-cyclo-6-aza-9-(benzyloxycarbonylamino)-10-methylundecanoic acid methyl ester (866395-28-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 72 percent / PhCO₂Ag; Et₃N / 2 h / Heating

2: LiBH₄ / tetrahydrofuran; H₂O / 1 h

3: AcOH / 80 °C

4: aq. NaOH / CH₂Cl₂ / 20 °C

5: 99 percent / Et₃N / CH₂Cl₂ / cooling

6: 71 percent / Et₃N / acetonitrile / 20 - 50 °C

With sodium hydroxide; lithium borohydride; silver benzoate; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; water; acetonitrile; 1: Wolff rearrangement;

DOI:10.1016/j.tet.2005.07.049

upstream raw materials:

(S)-1-mesyloxy-N-(benzyloxycarbonyl)-3-amino-4-methylpentane

methyl (2S)-pyrrolidine carboxylate

(S)-N-(benzyloxycarbonyl)-3-amino-4-methylpentan-1-ol

(R)-1-diazo-3-phthalimido-4-methylpentan-2-one

Downstream raw materials:

(2S,9S,12S,19S)-2,6-cyclo-12,16-cyclo-6,10,16-triaza-19-(benzyloxycarbonylamino)-20-methyl-11-oxo-9-(2'-propyl)heneicosanoic acid methyl ester

(2S,9S,12S)-2,6-cyclo-12,16-cyclo-6,10,16-triaza-19-(benzyloxycarbonylamino)-11-oxo-9-(2'-propyl)nonadecanoic acid methyl ester

(S)-1-((S)-3-Benzyloxycarbonylamino-4-methyl-pentyl)-pyrrolidine-2-carboxylic acid