L-N-Boc-ε-hydroxynorleucine benzylhydroxamate

Base Information

• Chemical Name: L-N-Boc-ε-hydroxynorleucine benzylhydroxamate
• CAS No.: 77611-38-2
• Molecular Formula: C₁₈H₂₈N₂O₅
• Molecular Weight: 352.431
• Mol file: 77611-38-2.mol

Synonyms:L-N-Boc-ε-hydroxynorleucine benzylhydroxamate

Chemical Property of L-N-Boc-ε-hydroxynorleucine benzylhydroxamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-N-Boc-ε-hydroxynorleucine benzylhydroxamate

There total 4 articles about L-N-Boc-ε-hydroxynorleucine benzylhydroxamate 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: 80.0%

O-benzylhydoxylamine hydrochloride (2687-43-6) + (S)-2-((tert-butoxycarbonyl)amino)-6-hydroxyhexanoic acid (77611-37-1) → L-N-Boc-ε-hydroxynorleucine benzylhydroxamate (77611-38-2)

Guidance literature:

With sodium hydroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In water; for 0.75h;

DOI:10.1021/ja00340a017

Reference yield: 80.0%

O-benzylhydoxylamine hydrochloride (2687-43-6) + α-N-(tert-butoxycarbonyl)-L-ε-hydroxynorleucine (77611-37-1,81505-64-8) → (1-Benzyloxycarbamoyl-5-hydroxy-pentyl)-carbamic acid tert-butyl ester (77611-38-2,84063-93-4)

Guidance literature:

With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In water; for 0.5h; Ambient temperature; pH 4.5;

DOI:10.1021/jo00326a061

Reference yield:

rac-6-hydroxynorleucine (5462-80-6) → (1-Benzyloxycarbamoyl-5-hydroxy-pentyl)-carbamic acid tert-butyl ester (77611-38-2,84063-93-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent

2: 80 percent / Et₃N / tetrahydrofuran; H₂O / Ambient temperature; overnight

3: 80 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide / H₂O / 0.5 h / Ambient temperature; pH 4.5

With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In tetrahydrofuran; water;

DOI:10.1021/jo00326a061

upstream raw materials:

O-benzylhydoxylamine hydrochloride

(S)-2-((tert-butoxycarbonyl)amino)-6-hydroxyhexanoic acid

α-N-(tert-butoxycarbonyl)-L-ε-hydroxynorleucine

rac-6-hydroxynorleucine

Downstream raw materials:

L-N_α-Boc-α-amino-N-(benzyloxy)caprolactame

{2-[(E)-Benzyloxyimino]-oxepan-3-yl}-carbamic acid tert-butyl ester

{2-[(Z)-Benzyloxyimino]-oxepan-3-yl}-carbamic acid tert-butyl ester

(1-Benzyloxy-2-oxo-azepan-3-yl)-carbamic acid tert-butyl ester

Refernces

• 1、 Maurer, Peter J.,Miller, Marvin J.. "Mycobactins: Synthesis of (-)-Cobactin T from ε-Hydroxynorleucine". . p. 2835 - 2836. Retrieved 2007/10/02.