((R)-4-tert-Butoxycarbonylamino-5-hydroxy-pentyl)-carbamic acid benzyl ester

Base Information

• Chemical Name: ((R)-4-tert-Butoxycarbonylamino-5-hydroxy-pentyl)-carbamic acid benzyl ester
• CAS No.: 252940-36-6
• Molecular Formula: C18H28N2O5
• Molecular Weight: 352.431
• Mol file: 252940-36-6.mol

Synonyms:((R)-4-tert-Butoxycarbonylamino-5-hydroxy-pentyl)-carbamic acid benzyl ester

Chemical Property of ((R)-4-tert-Butoxycarbonylamino-5-hydroxy-pentyl)-carbamic acid benzyl ester

Chemical Property:

• PSA: 103.87000
• LogP: 2.98740

Purity/Quality:

98% ^*data from raw suppliers

(R)-benzyltert-butyl(5-hydroxypentane-1,4-diyl)dicarbamate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ((R)-4-tert-Butoxycarbonylamino-5-hydroxy-pentyl)-carbamic acid benzyl ester

There total 1 articles about ((R)-4-tert-Butoxycarbonylamino-5-hydroxy-pentyl)-carbamic acid benzyl 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: 94.0%

(R)-Nδ-benzyloxycarbonyl-Nα-(tert-butoxycarbonyl)-ornithine (2480-93-5,16937-92-1) → (2R)-5-benzyloxycarbonylamino-2-tert-butyloxycarbonylaminopentan-1-ol (252940-36-6)

Guidance literature:

(R)-5-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)pentanoic acid; With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; at -15 ℃; for 0.0166667h;

With sodium tetrahydroborate; water; In tetrahydrofuran; at -15 ℃; for 0.166667h;

DOI:10.1021/jm060482a

Reference yield: 86.0%

(2R)-5-benzyloxycarbonylamino-2-tert-butyloxycarbonylaminopentan-1-ol (252940-36-6) → (2R)-5-(Benzyloxycarbonylamino)-2-amino-pentan-1-ol, hydrochloride (863963-92-2)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; dichloromethane; at 20 - 27 ℃;

Reference yield: 65.0%

3,5-dibromophenol (626-41-5) + (2R)-5-benzyloxycarbonylamino-2-tert-butyloxycarbonylaminopentan-1-ol (252940-36-6) → (R)-benzyl tert-butyl (5-(3,5-.dibromophenoxy)pentane-1,4-diyl)dicarbamate

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 16h;

upstream raw materials:

(R)-Nδ-benzyloxycarbonyl-Nα-(tert-butoxycarbonyl)-ornithine

Downstream raw materials:

thioacetic acid S-(5-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-pentyl) ester

(4-tert-butoxycarbonylamino-5-mercapto-pentyl)-carbamic acid benzyl ester

4-((R)-2-Amino-5-benzyloxycarbonylamino-pentylsulfanyl)-butyric acid

4-(5-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-pentylsulfanyl)-butyric acid tert-butyl ester

Refernces

• 1、 Martin, Olivier R.,Zhou, Wei,Wu, Xinfu,Front-Deschamps, Sophie,Moutel, Stéphane,Schindl, Katharina,Jeandet, Patricia,Zbaeren, Claude,Bauer, Jacques A.. "Synthesis and immunobiological activity of an original series of acyclic lipid A mimics based on a pseudodipeptide backbone". . p. 6000 - 6014. Retrieved 2007/10/03.