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

Base Information

• Chemical Name: N-(tert-butyloxycarbonyl)-L-valyl-L-valyl-N⁸-(benzyloxycarbonyl)-4(S),8-diamino-3(R)-hydroxyoctanoic acid ethyl ester
• CAS No.: 105617-27-4
• Molecular Formula: C₃₃H₅₄N₄O₉
• Molecular Weight: 650.813
• Mol file: 105617-27-4.mol

Synonyms:

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

There total 7 articles about N-(tert-butyloxycarbonyl)-L-valyl-L-valyl-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:

benzyl {(5S)-5-[(tert-butoxycarbonyl)amino]-6-oxohexyl}carbamate (82689-16-5) → N-(tert-butyloxycarbonyl)-L-valyl-L-valyl-N8-(benzyloxycarbonyl)-4(S),8-diamino-3(R)-hydroxyoctanoic acid ethyl ester (105617-27-4)

Guidance literature:

Multi-step reaction with 7 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

3: 54 percent / Cd, AcOH / dimethylformamide / 7 h / Ambient temperature

4: HCl / dioxane / 0.5 h / Ambient temperature

5: 1.) N-methylmorpholine / 1.) CHCl₂, 0 deg C, 2.) CHCl₂, from 0 deg C to RT, overnight

6: HCl / dioxane / 0.5 h / Ambient temperature

7: 1.) N-methylmorpholine / 1.) CHCl₂, 0 deg C, 2.) CHCl₂, from 0 deg C to RT, overnight

With 4-methyl-morpholine; pyridine; hydrogenchloride; dmap; acetic acid; cadmium; lithium diisopropyl amide; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/jm00385a010

Reference yield:

N4-(tert-butyl oxycarbonyl)-N8-(benzyloxycarbonyl)-4(S),8-diamino-3(R,S)-hydroxyoctanoic acid ethyl ester (98045-10-4,98063-00-4) → N-(tert-butyloxycarbonyl)-L-valyl-L-valyl-N8-(benzyloxycarbonyl)-4(S),8-diamino-3(R)-hydroxyoctanoic acid ethyl ester (105617-27-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 42 percent / 4-(N,N-dimethylamino)pyridine, pyridine / 0.33 h / Ambient temperature

2: 54 percent / Cd, AcOH / dimethylformamide / 7 h / Ambient temperature

3: HCl / dioxane / 0.5 h / Ambient temperature

4: 1.) N-methylmorpholine / 1.) CHCl₂, 0 deg C, 2.) CHCl₂, from 0 deg C to RT, overnight

5: HCl / dioxane / 0.5 h / Ambient temperature

6: 1.) N-methylmorpholine / 1.) CHCl₂, 0 deg C, 2.) CHCl₂, from 0 deg C to RT, overnight

With 4-methyl-morpholine; pyridine; hydrogenchloride; dmap; acetic acid; cadmium; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/jm00385a010

Reference yield:

N4-(tert-butyloxycarbonyl)-N8-(benzyloxycarbonyl)-4(S),8-diamino-3(R)-hydroxyoctanoic acid ethyl ester (98063-00-4) → N-(tert-butyloxycarbonyl)-L-valyl-L-valyl-N8-(benzyloxycarbonyl)-4(S),8-diamino-3(R)-hydroxyoctanoic acid ethyl ester (105617-27-4)

Guidance literature:

Multi-step reaction with 4 steps

1: HCl / dioxane / 0.5 h / Ambient temperature

2: 1.) N-methylmorpholine / 1.) CHCl₂, 0 deg C, 2.) CHCl₂, from 0 deg C to RT, overnight

3: HCl / dioxane / 0.5 h / Ambient temperature

4: 1.) N-methylmorpholine / 1.) CHCl₂, 0 deg C, 2.) CHCl₂, from 0 deg C to RT, overnight

With 4-methyl-morpholine; hydrogenchloride; In 1,4-dioxane;

DOI:10.1021/jm00385a010

upstream raw materials:

(S)-2-(tert-butoxycarbonylamino)-3-methylbutanoic anhydride

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

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

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

Downstream raw materials:

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