N⁴-(tert-butyloxycarbonyl)-N⁸-(benzyloxycarbonyl)-4(S),8-diamino-3(R)-hydroxyoctanoic acid ethyl ester

Base Information

• Chemical Name: N⁴-(tert-butyloxycarbonyl)-N⁸-(benzyloxycarbonyl)-4(S),8-diamino-3(R)-hydroxyoctanoic acid ethyl ester
• CAS No.: 105562-70-7
• Molecular Formula: C₂₆H₃₇Cl₃N₂O₉
• Molecular Weight: 627.947
• Mol file: 105562-70-7.mol

Synonyms:N⁴-(tert-butyloxycarbonyl)-N⁸-(benzyloxycarbonyl)-4(S),8-diamino-3(R)-hydroxyoctanoic acid ethyl ester

Chemical Property of N⁴-(tert-butyloxycarbonyl)-N⁸-(benzyloxycarbonyl)-4(S),8-diamino-3(R)-hydroxyoctanoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁴-(tert-butyloxycarbonyl)-N⁸-(benzyloxycarbonyl)-4(S),8-diamino-3(R)-hydroxyoctanoic acid ethyl ester

There total 2 articles about N⁴-(tert-butyloxycarbonyl)-N⁸-(benzyloxycarbonyl)-4(S),8-diamino-3(R)-hydroxyoctanoic acid ethyl 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: 42.0%

N4-(tert-butyl oxycarbonyl)-N8-(benzyloxycarbonyl)-4(S),8-diamino-3(R,S)-hydroxyoctanoic acid ethyl ester (98045-10-4,98063-00-4) + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → N4-(tert-butyloxycarbonyl)-N8-(benzyloxycarbonyl)-4(S),8-diamino-3(S)-hydroxyoctanoic acid ethyl ester (105562-69-4) + N4-(tert-butyloxycarbonyl)-N8-(benzyloxycarbonyl)-4(S),8-diamino-3(R)-hydroxyoctanoic acid ethyl ester (105562-70-7)

Guidance literature:

With pyridine; dmap; for 0.333333h; Ambient temperature;

DOI:10.1021/jm00385a010

Reference yield:

benzyl {(5S)-5-[(tert-butoxycarbonyl)amino]-6-oxohexyl}carbamate (82689-16-5) → N4-(tert-butyloxycarbonyl)-N8-(benzyloxycarbonyl)-4(S),8-diamino-3(R)-hydroxyoctanoic acid ethyl ester (105562-70-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LDA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, 25 min

2: 42 percent / 4-(N,N-dimethylamino)pyridine, pyridine / 0.33 h / Ambient temperature

With pyridine; dmap; lithium diisopropyl amide;

DOI:10.1021/jm00385a010

Reference yield: 54.0%

N4-(tert-butyloxycarbonyl)-N8-(benzyloxycarbonyl)-4(S),8-diamino-3(R)-hydroxyoctanoic acid ethyl ester (105562-70-7) → N4-(tert-butyloxycarbonyl)-N8-(benzyloxycarbonyl)-4(S),8-diamino-3(R)-hydroxyoctanoic acid ethyl ester (98063-00-4)

Guidance literature:

With acetic acid; cadmium; In N,N-dimethyl-formamide; for 7h; Ambient temperature;

DOI:10.1021/jm00385a010

upstream raw materials:

N⁴-(tert-butyl oxycarbonyl)-N⁸-(benzyloxycarbonyl)-4(S),8-diamino-3(R,S)-hydroxyoctanoic acid ethyl ester

2,2,2-Trichloroethyl chloroformate

benzyl {(5S)-5-[(tert-butoxycarbonyl)amino]-6-oxohexyl}carbamate

Downstream raw materials:

N⁴-(tert-butyloxycarbonyl)-N⁸-(benzyloxycarbonyl)-4(S),8-diamino-3(R)-hydroxyoctanoic acid ethyl ester

N-(tert-butyloxycarbonyl)-L-valyl-L-valyl-N⁸-(benzyloxycarbonyl)-4(S),8-diamino-3(R)-hydroxyoctanoic acid ethyl ester

N-(tert-butyloxycarbonyl)-L-valyl-N⁸-(benzyloxycarbonyl)-4(S),8-diamino-3(R)-hydroxyoctanoic acid ethyl ester

N-isovaleryl-L-valyl-L-valyl-N⁸-(benzyloxycarbonyl)-4(S),8-diamino-3(R)-hydroxyoctanoic acid ethyl ester