(2R)-2-[(tert-Butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl ester

Base Information

• Chemical Name: (2R)-2-[(tert-Butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl ester
• CAS No.: 210963-67-0
• Molecular Formula: C₁₇H₂₅NO₅
• Molecular Weight: 323.389
• DSSTox Substance ID: DTXSID701147226
• Nikkaji Number: J3.419.592G
• Mol file: 210963-67-0.mol

Synonyms:SCHEMBL3906191;GUUOABUKZOMRBA-CQSZACIVSA-N;DTXSID701147226;benzyl 2-(2R)-t-butoxycarbonylamino-5-hydroxypentanoate;benzyl N-(tert-butoxycarbonyl)-5-hydroxy-D-norvalinate;(2R)-2-[(tert-Butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl ester;N-[(1,1-Dimethylethoxy)carbonyl]-5-hydroxy-D-norvaline phenylmethyl ester;210963-67-0

Chemical Property of (2R)-2-[(tert-Butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl ester

Chemical Property:

• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 323.17327290
• Heavy Atom Count: 23
• Complexity: 372

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CCCO)C(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CCCO)C(=O)OCC1=CC=CC=C1

Technology Process of (2R)-2-[(tert-Butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl ester

There total 4 articles about (2R)-2-[(tert-Butoxycarbonyl)amino]-5-hydroxypentanoic 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: 82.0%

N-(tert-butoxycarbonyl)-D-glutamic acid 1-benzyl ester (34404-30-3) → (R)-N-tert-butoxycarbonyl-δ-hydroxynorvaline benzyl ester (210963-67-0)

Guidance literature:

N-(tert-butoxycarbonyl)-D-glutamic acid 1-benzyl ester; With chloroformic acid ethyl ester; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at -10 ℃; for 0.5h;

With sodium tetrahydroborate; In water; at 20 ℃; for 0.25h;

Reference yield:

(R)-2-tert-Butoxycarbonylamino-5-isobutoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester → (R)-N-tert-butoxycarbonyl-δ-hydroxynorvaline benzyl ester (210963-67-0)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at -10 - 20 ℃; for 0.75h;

DOI:10.1039/b411545g

Reference yield:

D-glutamic acid 1-benzyl ester (79338-14-0) → (R)-N-tert-butoxycarbonyl-δ-hydroxynorvaline benzyl ester (210963-67-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium carbonate / water; 1,4-dioxane / 2 h / 20 °C

2.1: chloroformic acid ethyl ester; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.5 h / -10 °C / Inert atmosphere

2.2: -10 °C

With chloroformic acid ethyl ester; potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1021/acs.joc.5b00532

upstream raw materials:

N-(tert-butoxycarbonyl)-D-glutamic acid 1-benzyl ester

D-glutamic acid 1-benzyl ester

di-tert-butyl dicarbonate