Boc-L-Serine-beta-Lactone

Base Information

• Chemical Name: Boc-L-Serine-beta-Lactone
• CAS No.: 98541-64-1
• Molecular Formula: C8H13NO4
• Molecular Weight: 187.196
• Hs Code.: 29322090
• DSSTox Substance ID: DTXSID50376803
• Nikkaji Number: J793.208A
• Wikidata: Q72510496
• ChEMBL ID: CHEMBL2064170
• Mol file: 98541-64-1.mol

Synonyms:98541-64-1;Boc-L-Serine-beta-Lactone;N-(tert-Butoxycarbonyl)-L-serine beta-Lactone;(S)-3-(tert-Butoxycarbonylamino)-2-oxetanone;(S)-tert-butyl (2-oxooxetan-3-yl)carbamate;tert-butyl N-[(3S)-2-oxooxetan-3-yl]carbamate;N-Boc-L-serine beta-Lactone;tert-butyl (S)-(2-oxooxetan-3-yl)carbamate;CHEMBL2064170;N-(tert-Butoxycarbonyl)-L-serine b-Lactone;(S)-N-(tert-Butoxycarbonyl)-3-amino-2-oxetanone;(S)-alpha-Boc-amino-beta-propiolactone;MFCD01318414;(S)-TERT-BUTYL 2-OXOOXETAN-3-YLCARBAMATE;(S)-3-BOC-AMINO-2-OXOOXETANE;[(3S)-2-oxo-3-oxetanyl]-1,1-dimethylethyl Ester Carbamic Acid;BOC-L-serine beta-lactone;N-Boc L-Serine ?-Lactone;N-Boc L-Serine beta-Lactone;SCHEMBL518197;(S)-alpha-tert-Butoxycarbonylamino-beta-propiolactone;N-Boc L-Serine beta -Lactone;AMY7763;DTXSID50376803;HRJDEHQWXAPGBG-YFKPBYRVSA-N;BDBM50389013;Carbamic acid, [(3S)-2-oxo-3-oxetanyl]-, 1,1-dimethylethyl ester;AKOS015838050;CS-W016860;GS-6419;AC-23830;B1995;(S)-tert-butoxycarbonylamino-beta-propiolactone;tert-Butyl [(3S)-2-oxooxetan-3-yl]carbamate;N-Boc-L-serine beta-lactone, >=96.0% (GC);(S)-(2-oxooxetan-3-yl)carbamic acid tert-butyl ester;2-Methyl-2-propanyl [(3S)-2-oxo-3-oxetanyl]carbamate;(S)-tert-butyl 2-oxooxetan-3-ylcarbamate

Chemical Property of Boc-L-Serine-beta-Lactone

Chemical Property:

• Vapor Pressure: 0.000349mmHg at 25°C
• Melting Point: 117-119 °C
• Refractive Index: -26 ° (C=1, CH3CN)
• Boiling Point: 319 °C at 760 mmHg
• PKA: 10.53±0.20(Predicted)
• Flash Point: 146.7 °C
• PSA: 64.63000
• Density: 1.18 g/cm³
• LogP: 0.82740
• Storage Temp.: Freezer
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly), DMSO (Slightly), Methanol(Slightly)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 187.08445790
• Heavy Atom Count: 13
• Complexity: 231

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-Boc L-Serine b-Lactone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1COC1=O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H]1COC1=O
• Uses: An important -lactone inhibitor

Technology Process of Boc-L-Serine-beta-Lactone

There total 10 articles about Boc-L-Serine-beta-Lactone 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: 87.7%

(S)-N-(tert-butoxycarbonyl)serine (3262-72-4) → (S)-3-(tert-butoxycarbonylamino)-oxetan-2-one (98541-64-1)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/j.bmc.2006.11.015

Reference yield: 84.0%

(R)-N-tert-butoxycarbonyl serine (3262-72-4,3850-40-6,6368-20-3,90582-28-8,84311-18-2) → N-(tert-butyloxycarbonyl)-D-serine β-lactone (98541-64-1,132340-68-2,126330-77-6)

Guidance literature:

With dimethyl azodicarboxylate; triphenylphosphine; In acetonitrile; at -65 ℃; for 1.5h;

DOI:10.1021/jo9520194

Reference yield: 57.0%

tert-butyl (2S)-1-hydroxy-3-oxobutan-2-ylcarbamate (1013028-29-9,477191-17-6) → N-(tert-butyloxycarbonyl)-D-serine β-lactone (98541-64-1,132340-68-2,126330-77-6)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/j.ejmech.2021.113785

upstream raw materials:

(R)-N-tert-butoxycarbonyl serine

(S)-N-(tert-butoxycarbonyl)serine

di-tert-butyl dicarbonate

tert-butyl (2S)-1-hydroxy-3-oxobutan-2-ylcarbamate

Downstream raw materials:

N-(tert-butoxycarbonyl)-3-imidazol-1-yl-L-alanine

N²-tertbutoxycarbonyl-D-2,3-diaminopropanoic acid

N²-tertbutoxycarbonyl-L-2,3-diaminopropanoic acid

(R)-2-tert-Butoxycarbonylamino-3-((R)-2-tert-butoxycarbonylamino-3-hydroxy-propionylamino)-propionic acid

Refernces

• 1、 Paradis-Bleau, Catherine,Beaumont, Melanie,Sanschagrin, Francois,Voyer, Normand,Levesque, Roger C.. "Parallel solid synthesis of inhibitors of the essential cell division FtsZ enzyme as a new potential class of antibacterials". . p. 1330 - 1340. Retrieved 2007.
• 2、 Gu, Weijie,Martinez, Sergio,Singh, Abhimanyu K.,Nguyen, Hoai,Rozenski, Jef,Schols, Dominique,Herdewijn, Piet,Das, Kalyan,De Jonghe, Steven. "Exploring the dNTP -binding site of HIV-1 reverse transcriptase for inhibitor design". . . Retrieved 2021/08/24.
• 3、 Singh, Puspendra,Singh, Harkesh B.,Butcher, Ray J.. "Synthesis and characterization of selenium(I/II) and tellurium(IV) derivatives of amino acids". . p. 1 - 9. Retrieved 2018/09/21.