N-ALPHA-BENZYLOXYCARBONYL-N-ALPHA-METHYL-O-ACETYL-L-SERINE DICYCLOHEXYLAMINE

Base Information

• Chemical Name: N-ALPHA-BENZYLOXYCARBONYL-N-ALPHA-METHYL-O-ACETYL-L-SERINE DICYCLOHEXYLAMINE
• CAS No.: 519156-35-5
• Molecular Formula: C14H17NO6
• Molecular Weight: 476.61
• Mol file: 519156-35-5.mol

Synonyms:N-ALPHA-BENZYLOXYCARBONYL-N-ALPHA-METHYL-O-ACETYL-L-SERINE DICYCLOHEXYLAMINE;Z-L-MESER(AC)-OH DCHA

Chemical Property of N-ALPHA-BENZYLOXYCARBONYL-N-ALPHA-METHYL-O-ACETYL-L-SERINE DICYCLOHEXYLAMINE

Chemical Property:

• PSA: 93.14000
• LogP: 1.27130

Purity/Quality:

98.5% ^*data from raw suppliers

N-ALPHA-BENZYLOXYCARBONYL-N-ALPHA-METHYL-O-ACETYL-L-SERINE DICYCLOHEXYLAMINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-ALPHA-BENZYLOXYCARBONYL-N-ALPHA-METHYL-O-ACETYL-L-SERINE DICYCLOHEXYLAMINE

There total 2 articles about N-ALPHA-BENZYLOXYCARBONYL-N-ALPHA-METHYL-O-ACETYL-L-SERINE DICYCLOHEXYLAMINE 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: 88.0%

phenylmethyl (4S)-4-[(acetyloxy)methyl]-5-oxo-1,3-oxazolidine-3-carboxylate (519156-33-3) → (2S)-3-(acetyloxy)-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)propanoic acid (519156-35-5)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In chloroform; at 20 ℃; for 96.2h;

DOI:10.1021/acs.jmedchem.1c00347

Reference yield:

(S)-3-acetoxy-2-(benzyloxycarbonylamino)propanoic acid (19645-29-5) → (2S)-3-(acetyloxy)-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)propanoic acid (519156-35-5)

Guidance literature:

Multi-step reaction with 2 steps

1: CSA / toluene / Heating

2: Et₃SiH; CF₃COOH / CH₂Cl₂

With triethylsilane; trifluoroacetic acid; camphor-10-sulfonic acid; In dichloromethane; toluene;

DOI:10.1002/hlca.200690235

Reference yield: 74.0%

N-cyclohexyl-cyclohexanamine (101-83-7) + (2S)-3-(acetyloxy)-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)propanoic acid (519156-35-5) → N-benzyloxycarbonyl-N-methyl-L-serine-O-acetate dicyclohexylamine salt

Guidance literature:

In diethyl ether;

upstream raw materials:

phenylmethyl (4S)-4-[(acetyloxy)methyl]-5-oxo-1,3-oxazolidine-3-carboxylate

(S)-3-acetoxy-2-(benzyloxycarbonylamino)propanoic acid

Downstream raw materials:

(2S)-4-diazo-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)-3-oxobutyl acetate

(3R)-4-(acetyloxy)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)butanoic acid