Benzyl-N-(tert-butyloxycarbonyl)-O-benzyl-(S)-serinehydroxamate

Base Information

• Chemical Name: Benzyl-N-(tert-butyloxycarbonyl)-O-benzyl-(S)-serinehydroxamate
• CAS No.: 79722-11-5
• Molecular Formula: C₂₂H₂₈N₂O₅
• Molecular Weight: 400.475
• Mol file: 79722-11-5.mol

Synonyms:Benzyl-N-(tert-butyloxycarbonyl)-O-benzyl-(S)-serinehydroxamate

Chemical Property of Benzyl-N-(tert-butyloxycarbonyl)-O-benzyl-(S)-serinehydroxamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl-N-(tert-butyloxycarbonyl)-O-benzyl-(S)-serinehydroxamate

There total 3 articles about Benzyl-N-(tert-butyloxycarbonyl)-O-benzyl-(S)-serinehydroxamate 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%

BOC-O-benzyl-L-serine (23680-31-1) + O-benzylhydoxylamine hydrochloride (2687-43-6) → Benzyl-N-(tert-butyloxycarbonyl)-O-benzyl-(S)-serinehydroxamate (79722-11-5)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1021/jo00074a038

Reference yield: 82.0%

N-benzyloxyamine (622-33-3) + BOC-O-benzyl-L-serine (23680-31-1) → Benzyl-N-(tert-butyloxycarbonyl)-O-benzyl-(S)-serinehydroxamate (79722-11-5)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; water; 1) 0 deg C, 3 h, 2) r.t., overnight;

DOI:10.1021/jo00339a047

Reference yield:

O-benzylhydoxylamine hydrochloride (2687-43-6) + Boc-L-Ser(Bzl)-OBt (129297-17-2) → Benzyl-N-(tert-butyloxycarbonyl)-O-benzyl-(S)-serinehydroxamate (79722-11-5)

Guidance literature:

O-benzylhydoxylamine hydrochloride; With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; for 0.166667h; Inert atmosphere;

Boc-L-Ser(Bzl)-OBt; In tetrahydrofuran; dichloromethane; Inert atmosphere;

DOI:10.1039/c2ob26010g

upstream raw materials:

N-benzyloxyamine

BOC-O-benzyl-L-serine

O-benzylhydoxylamine hydrochloride

Boc-L-Ser(Bzl)-OBt

Downstream raw materials:

O,O-Dibenzyl-N-(tert-butyloxycarbonyl)-(S)-norneoenactin A

O,O-Dibenzyl-N-(tert-butyloxycarbonyl)neoenactin A

(L,L)-N-α-Boc-N-δ-benzyloxy-N-δ-[N-α-Boc-3-(O-benzyl)serinyl]ornithine benzyl ester

C₃₉H₅₁N₃O₉

Refernces

• 1、 Darwish,Patel,Miller. "Synthesis of the antifungal agent norneoenactin A". . p. 6072 - 6075. Retrieved 2007/10/02.