(2R,3S,4R)-4-(N-(((tert)-butyloxy)carbonyl)-amino)-2-amino-3-hydroxy-1-(1-naphthyl)-5-phenylpentane acetonide

Base Information

• Chemical Name: (2R,3S,4R)-4-(N-(((tert)-butyloxy)carbonyl)-amino)-2-amino-3-hydroxy-1-(1-naphthyl)-5-phenylpentane acetonide
• CAS No.: 148472-73-5
• Molecular Formula: C₂₉H₃₆N₂O₃
• Molecular Weight: 460.616
• Mol file: 148472-73-5.mol

Synonyms:(2R,3S,4R)-4-(N-(((tert)-butyloxy)carbonyl)-amino)-2-amino-3-hydroxy-1-(1-naphthyl)-5-phenylpentane acetonide

Chemical Property of (2R,3S,4R)-4-(N-(((tert)-butyloxy)carbonyl)-amino)-2-amino-3-hydroxy-1-(1-naphthyl)-5-phenylpentane acetonide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R)-4-(N-(((tert)-butyloxy)carbonyl)-amino)-2-amino-3-hydroxy-1-(1-naphthyl)-5-phenylpentane acetonide

There total 6 articles about (2R,3S,4R)-4-(N-(((tert)-butyloxy)carbonyl)-amino)-2-amino-3-hydroxy-1-(1-naphthyl)-5-phenylpentane acetonide 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: 78.0%

(2R,3S,4R)-4-(N-(((tert)-butyloxy)carbonyl)-amino)-2-(N-((benzyloxy)carbonyl)-amino)-3-hydroxy-1-(1-naphthyl)-5-phenylpentane acetonide (148472-70-2) → (2R,3S,4R)-4-(N-(((tert)-butyloxy)carbonyl)-amino)-2-amino-3-hydroxy-1-(1-naphthyl)-5-phenylpentane acetonide (148472-73-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetic acid; for 21h;

DOI:10.1016/S0040-4020(01)80342-2

Reference yield:

(4S,5R)-N-(((tert)-butyloxy)carbonyl)-5-benzyl-4-hydroxy-2-pyrrolidinone (109579-10-4,109579-13-7,144186-19-6) → (2R,3S,4R)-4-(N-(((tert)-butyloxy)carbonyl)-amino)-2-amino-3-hydroxy-1-(1-naphthyl)-5-phenylpentane acetonide (148472-73-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) HMPA, 2) (1-C₁₀H₇)CH₂Br / 1) THF, -78 degC, 50 min, 2) THF, -78 degC, 30 min

2: 1) 1M LiOH, 2) PPTS / 1) THF, 1.5 h, 2) CH₂Cl₂, r.t., 2 h

3: diphenylphosphoryl azide, Et₃N / xylene / 2 h / 90 °C

4: DMAP / 15 h

5: 78 percent / H₂ / 10percent Pd/C / acetic acid / 21 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; (1-C₁₀H₇)CH₂Br; diphenylphosphoranyl azide; hydrogen; pyridinium p-toluenesulfonate; triethylamine; palladium on activated charcoal; In acetic acid; xylene;

DOI:10.1016/S0040-4020(01)80342-2

Reference yield:

(3R,4S,5R)-N-(((tert)-butyloxy)carbonyl)-5-benzyl-4-hydroxy-3-(1-naphthylmethyl)-2-pyrrolidinone (148554-95-4) → (2R,3S,4R)-4-(N-(((tert)-butyloxy)carbonyl)-amino)-2-amino-3-hydroxy-1-(1-naphthyl)-5-phenylpentane acetonide (148472-73-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) 1M LiOH, 2) PPTS / 1) THF, 1.5 h, 2) CH₂Cl₂, r.t., 2 h

2: diphenylphosphoryl azide, Et₃N / xylene / 2 h / 90 °C

3: DMAP / 15 h

4: 78 percent / H₂ / 10percent Pd/C / acetic acid / 21 h

With dmap; lithium hydroxide; diphenylphosphoranyl azide; hydrogen; pyridinium p-toluenesulfonate; triethylamine; palladium on activated charcoal; In acetic acid; xylene;

DOI:10.1016/S0040-4020(01)80342-2

upstream raw materials:

(2R,3S,4R)-4-(N-(((tert)-butyloxy)carbonyl)-amino)-2-(N-((benzyloxy)carbonyl)-amino)-3-hydroxy-1-(1-naphthyl)-5-phenylpentane acetonide

(4S,5R)-N-(((tert)-butyloxy)carbonyl)-5-benzyl-4-hydroxy-2-pyrrolidinone

(3R,4S,5R)-N-(((tert)-butyloxy)carbonyl)-5-benzyl-4-hydroxy-3-(1-naphthylmethyl)-2-pyrrolidinone

(2R,3S,4R)-4-(N-(((tert)-butyloxy)carbonyl)-amino)-3-hydroxy-2-(1-naphthylmethyl)-5-phenylpentanoic acid acetonide