benzyl tert-butyl(1s,2s)-cyclopentane-1,2-diyldicarbaMate

Base Information

• Chemical Name: benzyl tert-butyl(1s,2s)-cyclopentane-1,2-diyldicarbaMate
• CAS No.: 815645-22-8
• Molecular Formula: C18H26N2O4
• Molecular Weight: 334.415
• Mol file: 815645-22-8.mol

Synonyms:Benzyl tert-butyl (1S,2S)-cyclopentane-1,2-diyldicarbamate;

Chemical Property of benzyl tert-butyl(1s,2s)-cyclopentane-1,2-diyldicarbaMate

Chemical Property:

• PSA: 76.66000
• LogP: 4.14040
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

Benzyltert-butyl(1S,2S)-cyclopentane-1,2-diyldicarbamate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of benzyl tert-butyl(1s,2s)-cyclopentane-1,2-diyldicarbaMate

There total 3 articles about benzyl tert-butyl(1s,2s)-cyclopentane-1,2-diyldicarbaMate 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: 89.0%

benzyl alcohol (100-51-6,185532-71-2) + (1S,2S)-2-(tert-butoxycarbonylamino)cyclopentyl isocyanate (815645-21-7) → tert-butyl (1S,2S)-2-(benzyloxycarbonylamino)cyclopentylcarbamate (815645-22-8)

Guidance literature:

With copper(l) chloride; In N,N-dimethyl-formamide; at 20 ℃; for 0.75h;

DOI:10.1021/ja046280q

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (1S,2S)-2-(benzyloxycarbonylamino)cyclopentylcarbamate (815645-22-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Et₃N; ethyl chloroformate / tetrahydrofuran / 0.33 h / 0 °C

1.2: aq. NaN₃ / tetrahydrofuran / 0.33 h / 0 °C

2.1: 2.15 g / benzene / 0.5 h / Heating

3.1: 89 percent / CuCl / dimethylformamide / 0.75 h / 20 °C

With chloroformic acid ethyl ester; triethylamine; copper(l) chloride; In tetrahydrofuran; N,N-dimethyl-formamide; benzene; 3.1: Curtius rearrangement;

DOI:10.1021/ja046280q

Reference yield:

((1S,2S)-2-Azidocarbonyl-cyclopentyl)-carbamic acid tert-butyl ester → tert-butyl (1S,2S)-2-(benzyloxycarbonylamino)cyclopentylcarbamate (815645-22-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.15 g / benzene / 0.5 h / Heating

2: 89 percent / CuCl / dimethylformamide / 0.75 h / 20 °C

With copper(l) chloride; In N,N-dimethyl-formamide; benzene; 1: Curtius rearrangement;

DOI:10.1021/ja046280q

upstream raw materials:

benzyl alcohol

(1S,2S)-2-(tert-butoxycarbonylamino)cyclopentyl isocyanate

di-tert-butyl dicarbonate

Downstream raw materials:

methyl N-[(2S)-tert-butoxycarbonylaminocyclopent-(1S)-yl]-N-[6-N-(benzyloxycarbonyl)adenin-9-ylacetyl]glycinate

methyl N-[(2S)-tert-butoxycarbonylaminocyclopent-(1S)-yl]-N-[4-N-(benzyloxycarbonyl)cytosin-1-ylacetyl]glycinate

(-)-(1S,2S)-N-mono(tert-butoxycarbonyl) cyclopentane-1,2-diamine

Refernces