2(3H)-Furanone, 5-(azidomethyl)dihydro-, (S)-

Base Information

• Chemical Name: 2(3H)-Furanone, 5-(azidomethyl)dihydro-, (S)-
• CAS No.: 24211-53-8
• Molecular Formula: C5H7N3O2
• Molecular Weight: 141.129
• DSSTox Substance ID: DTXSID20456065
• Nikkaji Number: J748.675H
• Wikidata: Q82278271
• Mol file: 24211-53-8.mol

Synonyms:(5S)-5-(azidomethyl)oxolan-2-one;24211-53-8;2(3H)-Furanone, 5-(azidomethyl)dihydro-, (S)-;CTK0I7540;SCHEMBL23592803;DTXSID20456065;(4S)-4-Hydroxy-5-azidopentanoic acid lactone

Chemical Property of 2(3H)-Furanone, 5-(azidomethyl)dihydro-, (S)-

Chemical Property:

• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 141.053826475
• Heavy Atom Count: 10
• Complexity: 185

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)OC1CN=[N+]=[N-]
• Isomeric SMILES: C1CC(=O)O[C@@H]1CN=[N+]=[N-]

Technology Process of 2(3H)-Furanone, 5-(azidomethyl)dihydro-, (S)-

There total 1 articles about 2(3H)-Furanone, 5-(azidomethyl)dihydro-, (S)- 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:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → (S)-(+)-5-Azidomethyl-2-oxotetrahydrofuran (24211-53-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / pyridine, N,N-dimethylaminopyridine

2: 87 percent / sodium azide / 1 h / Heating

With pyridine; dmap; sodium azide;

DOI:10.1021/jo00206a040

Reference yield: 98.0%

(S)-(+)-5-Azidomethyl-2-oxotetrahydrofuran (24211-53-8) → (S)-5-hydroxypiperidin-2-one (24211-54-9)

Guidance literature:

With 20% palladium hydroxide-activated charcoal; hydrogen; In methanol; at 25 ℃; for 24h; under 760.051 Torr;

DOI:10.1080/00397911.2015.1033428

Reference yield:

(S)-(+)-5-Azidomethyl-2-oxotetrahydrofuran (24211-53-8) → (S)-3-hydroxypiperidine (24211-55-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / H₂ / 5percent Pd/C / methanol / 2585.7 Torr

2: 68 percent / diborane / tetrahydrofuran; hexane / 2 h / Heating

With hydrogen; diborane; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane;

DOI:10.1021/jo00206a040

upstream raw materials:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

Downstream raw materials:

(R)-(+)-5-Hydroxy-2-oxopiperidine

(S)-5-hydroxypiperidin-2-one

N-[1-(2'-azido-1'(S)-hydroxy)butylcarboxy]-L-phenylalanyl-L-leucine

N-[1-(2'-azido-1'(S)-hydroxy)butylcarboxy]-L-phenylalanyl-L-leucyl methyl ester

Refernces

• 1、 Herdeis. "Chirospecific synthesis of (S)-(+)- and (R)-(-)-5-amino-4- hydroxypentanoic acid from L- and D-glutamic acid via (S)-(+)- and (R)-(-)-5-hydroxy-2-oxopiperidine". . p. 232 - 233. Retrieved 2007/10/02.