Ethyl 3-azido-2-hydroxy-propionate

Base Information

• Chemical Name: Ethyl 3-azido-2-hydroxy-propionate
• CAS No.: 144787-20-2
• Molecular Formula: C5H9N3O3
• Molecular Weight: 235.243
• DSSTox Substance ID: DTXSID20448884
• Wikidata: Q82268076
• Mol file: 144787-20-2.mol

Synonyms:144787-20-2;ETHYL 3-AZIDO-2-HYDROXY-PROPIONATE;ETHYL (2R,3S)-3-AZIDO-2-HYDROXY-3-PHENYLPROPANOATE;CTK8F9604;DTXSID20448884

Chemical Property of Ethyl 3-azido-2-hydroxy-propionate

Chemical Property:

• PSA: 96.28000
• LogP: 1.41476
• Solubility.: Chloroform, Ethyl Acetate
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 235.09569129
• Heavy Atom Count: 17
• Complexity: 296

Purity/Quality:

Ethyl3-Azido-2-hydroxy-propionate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C(C1=CC=CC=C1)N=[N+]=[N-])O
• Isomeric SMILES: CCOC(=O)[C@@H]([C@H](C1=CC=CC=C1)N=[N+]=[N-])O
• Uses: Ethyl 3-Azido-2-hydroxy-propionate (cas# 144787-20-2) is a compound useful in organic synthesis.

Technology Process of Ethyl 3-azido-2-hydroxy-propionate

There total 17 articles about Ethyl 3-azido-2-hydroxy-propionate 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: 99.0%

ethyl (2R,3R)-3-phenyl-2,3-oxiranepropanoate (126060-73-9) → (2R,3S)-3-azido-2-hydroxy-benzenepropanoic acid ethyl ester (144787-20-2)

Guidance literature:

With sodium azide; ammonium chloride; In ethanol; at 60 ℃; for 8h;

DOI:10.1016/S0040-4039(00)79128-3

Reference yield: 95.0%

(2R,3S)-ethyl 3-phenylglycidate (2272-55-1) → (2R,3S)-3-azido-2-hydroxy-benzenepropanoic acid ethyl ester (144787-20-2)

Guidance literature:

With sodium azide; ammonium chloride; In methanol; at 65 ℃; for 6h;

DOI:10.3390/molecules19068067

Reference yield: 85.0%

ethyl (2S,3R)-3-bromo-2-hydroxy-3-phenylpropionate (246861-67-6) → (2R,3S)-3-azido-2-hydroxy-benzenepropanoic acid ethyl ester (144787-20-2)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 60 ℃; for 12h;

upstream raw materials:

ethyl (2R,3R)-3-phenyl-2,3-oxiranepropanoate

ethyl (2S,3R)-3-bromo-2-hydroxy-3-phenylpropionate

(2R,3S)-ethyl 2,3-dihydroxy-3-phenylpropanoate

ethyl (4S,5R)-4-carbethoxy-5-phenyl-1,3,2-dioxathiolane-2-oxide

Downstream raw materials:

(2R,3S)-3-amino-3-phenyl-2-hydroxypropionic acid ethyl ester

(2R,3S) ethyl N-(t-butoxycarbonyl)-3-phenylisoserine

ethyl (2R,3S)-3-azido-2-O-benzoyl-3-phenylpropionate

ethyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate