(2S,3R)-3-benzyloxycarbonylamino-2-hydroxyoctanoic acid

Base Information

• Chemical Name: (2S,3R)-3-benzyloxycarbonylamino-2-hydroxyoctanoic acid
• CAS No.: 184652-42-4
• Molecular Formula: C₁₆H₂₃NO₅
• Molecular Weight: 309.362
• Mol file: 184652-42-4.mol

Synonyms:(2S,3R)-3-benzyloxycarbonylamino-2-hydroxyoctanoic acid

Chemical Property of (2S,3R)-3-benzyloxycarbonylamino-2-hydroxyoctanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-3-benzyloxycarbonylamino-2-hydroxyoctanoic acid

There total 2 articles about (2S,3R)-3-benzyloxycarbonylamino-2-hydroxyoctanoic acid 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: 98.5%

(2S,3R)-3-amino-2-hydroxyoctanoic acid (154702-01-9) + 2-benzyloxycarbonylsulfanyl-4,6-dimethyl-pyrimidine (42116-21-2) → (2S,3R)-3-benzyloxycarbonylamino-2-hydroxyoctanoic acid (184652-42-4)

Guidance literature:

With triethylamine; In 1,4-dioxane; for 23h; Ambient temperature;

DOI:10.7164/antibiotics.49.1031

Reference yield:

(4R,5S)-ethyl 2-oxo-4-pentyloxazolidine-5-carboxylate (184652-41-3) → (2S,3R)-3-benzyloxycarbonylamino-2-hydroxyoctanoic acid (184652-42-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 97.7 percent / NaOH / ethanol / 9 h / Heating

2: 98.5 percent / Et₃N / dioxane / 23 h / Ambient temperature

With sodium hydroxide; triethylamine; In 1,4-dioxane; ethanol;

DOI:10.7164/antibiotics.49.1031

Reference yield: 88.8%

N-p-Toluolsulfonyl-L-phenylalanin-benzylester (67850-39-9) + (2S,3R)-3-benzyloxycarbonylamino-2-hydroxyoctanoic acid (184652-42-4) → (2S,3R)-3-benzyloxycarbonylamino-2-hydroxyoctanoyl-L-phenylalanine benzyl ester (184652-46-8)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; for 21h; Ambient temperature;

DOI:10.7164/antibiotics.49.1031

upstream raw materials:

(2S,3R)-3-amino-2-hydroxyoctanoic acid

2-benzyloxycarbonylsulfanyl-4,6-dimethyl-pyrimidine

(4R,5S)-ethyl 2-oxo-4-pentyloxazolidine-5-carboxylate

Downstream raw materials:

(2S,3R)-3-benzyloxycarbonylamino-2-hydroxyoctanoyl-L-alanine benzyl ester

(2S,3R)-3-benzyloxycarbonylamino-2-hydroxyoctanoyl-L-valine benzyl ester

(2S,3R)-3-benzyloxycarbonylamino-2-hydroxyoctanoyl-L-leucine benzyl ester

(2S,3R)-3-benzyloxycarbonylamino-2-hydroxyoctanoyl-L-phenylalanine benzyl ester

Refernces