(4-tert-ButoxycarbonylaMino-1-hydroxyMethyl-butyl)-carbaMic acid benzyl ester

Base Information

• Chemical Name: (4-tert-ButoxycarbonylaMino-1-hydroxyMethyl-butyl)-carbaMic acid benzyl ester
• CAS No.: 849815-16-3
• Molecular Formula: C18H28N2O5
• Molecular Weight: 352.431
• Mol file: 849815-16-3.mol

Synonyms:Carbamic acid, [(1S)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-1-(hydroxymethyl)butyl]-, phenylmethyl ester;(4-tert-Butoxycarbonylamino-1-hydroxymethyl-butyl)-carbamic acid benzyl ester;Benzyl tert-butyl (5-hydroxypentane-1,4-diyl)dicarbamate;

Chemical Property of (4-tert-ButoxycarbonylaMino-1-hydroxyMethyl-butyl)-carbaMic acid benzyl ester

Chemical Property:

• Boiling Point: 542.0±50.0 °C(Predicted)
• PKA: 11.82±0.46(Predicted)
• PSA: 96.89000
• Density: 1.137±0.06 g/cm3(Predicted)
• LogP: 3.36040

Purity/Quality:

97% ^*data from raw suppliers

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 (4-tert-ButoxycarbonylaMino-1-hydroxyMethyl-butyl)-carbaMic acid benzyl ester

There total 5 articles about (4-tert-ButoxycarbonylaMino-1-hydroxyMethyl-butyl)-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: 97.0%

Nα-(benzyloxycarbonyl)-Nδ-(tert-butoxycarbonyl)-L-ornithine methyl ester (32393-52-5) → tert-butyl N-[(4S)-4-(benzyloxycarbonylamino)-5-hydroxy-pentyl]carbamate (849815-16-3)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; at 0 - 20 ℃; for 0.5h;

Reference yield: 79.0%

Z-Orn(Boc)-OH (7733-29-1,199924-46-4) → tert-butyl N-[(4S)-4-(benzyloxycarbonylamino)-5-hydroxy-pentyl]carbamate (849815-16-3)

Guidance literature:

Z-Orn(Boc)-OH; With 4-methyl-morpholine; isobutyl chloroformate; In 1,2-dimethoxyethane; at -15 - -10 ℃; for 0.25h;

With sodium tetrahydroborate; water; In 1,2-dimethoxyethane; at -15 ℃; for 0.166667h;

Reference yield: 16.0%

(2S)-2-benzyloxycarbonylamino-5-tert-butoxycarbonylaminopentane-1-sulfamate (1146698-93-2) → tert-butyl N-[(4S)-4-(benzyloxycarbonylamino)-5-hydroxy-pentyl]carbamate (849815-16-3) + 4-(3-tert-butoxycarbonylamino)propyl-2,2-dioxo-1,2,3-oxathiazole (1211773-89-5) + (4S)-4-(3-tert-butoxycarbonylamino)propyl-2-oxazolidinone (1211773-92-0) + (4S,5S)-5-benzyloxycarbonylamino-4-(2-tert-butoxycarbonylamino)ethyl-2,2-dioxo-1,2,3-oxathiazinane (1146698-96-5) + (4R,5S)-5-benzyloxycarbonylamino-4-(2-tert-butoxycarbonylamino)ethyl-2,2-dioxo-1,2,3-oxathiazinane (1146698-95-4) + (5S,8R)-9-benzyloxycarbonyl-8-tert-butoxycarbonylamino-2,2-dioxo-9-iminobicyclo[3,3,1]-1,2,3-oxathiazecane (1211773-91-9)

Guidance literature:

With [bis(acetoxy)iodo]benzene; bis[rhodium(α,α,α',α'-tetramethyl-1,3-benzenedipropionic acid)]; magnesium oxide; In dichloromethane; at 40 ℃; for 1.5h;

DOI:10.1021/jo9027193

upstream raw materials:

chloroformic acid ethyl ester

(2S)-2-benzyloxycarbonylamino-5-tert-butoxycarbonylaminopentane-1-sulfamate

N^α-(benzyloxycarbonyl)-N^δ-(tert-butoxycarbonyl)-L-ornithine methyl ester

Z-Orn(Boc)-OH

Downstream raw materials:

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

(2S)-2-benzyloxycarbonylamino-5-tert-butoxycarbonylaminopentane-1-sulfamate

(S)-benzyl tert-butyl (5-aminopentane-1,4-diyl)dicarbamate