(S)-3-(Hydroxymethyl)piperazine-2,5-dione

Base Information

• Chemical Name: (S)-3-(Hydroxymethyl)piperazine-2,5-dione
• CAS No.: 52661-98-0
• Molecular Formula: C5H8N2O3
• Molecular Weight: 144.13
• DSSTox Substance ID: DTXSID20428621
• Nikkaji Number: J1.560.245G
• Wikidata: Q72459516
• Mol file: 52661-98-0.mol

Synonyms:52661-98-0;CYCLO(-GLY-SER);(S)-3-(Hydroxymethyl)piperazine-2,5-dione;(3S)-3-(hydroxymethyl)piperazine-2,5-dione;Cyclo(Gly-Ser-);CYCLO(GLY-L-SER);Cyclo(-Gly-Ser), AldrichCPR;SCHEMBL17966443;DTXSID20428621;MFCD00237615;AKOS006275242;BS-28601;CS-0046698;A870935

Chemical Property of (S)-3-(Hydroxymethyl)piperazine-2,5-dione

Chemical Property:

• PSA: 78.43000
• LogP: -1.74910
• Storage Temp.: -15°C
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 144.05349212
• Heavy Atom Count: 10
• Complexity: 168

Purity/Quality:

99%+, ^*data from raw suppliers

Cyclo(-Gly-Ser) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(=O)NC(C(=O)N1)CO
• Isomeric SMILES: C1C(=O)N[C@H](C(=O)N1)CO

Technology Process of (S)-3-(Hydroxymethyl)piperazine-2,5-dione

There total 9 articles about (S)-3-(Hydroxymethyl)piperazine-2,5-dione 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: 100.0%

C16H27N3O5 → 3-hydroxymethyl-2,5-diketopiperazine (89181-64-6,52661-98-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1002/ejoc.202001671

Reference yield: 96.0%

O-(tert-butyl)-L-serylglycine (20994-69-8) → cyclo(glycyl-L-seryl) (52661-98-0)

Guidance literature:

With (3-{[(cyclohexylimino)methylidene]amino}propyl)oxy linked polystyrene resin; In dichloromethane; N,N-dimethyl-formamide; for 0.0833333h; Flow reactor;

DOI:10.1021/acscombsci.0c00001

Reference yield: 92.0%

Gly-Ser (7361-43-5,82660-87-5) → cyclo(glycyl-L-seryl) (52661-98-0)

Guidance literature:

With 14C₂H₇N*14H⁽¹⁺⁾*2H₂O*2O^(2-)*2Zr⁽⁴⁺⁾*O₁₂₂P₄W₃₄^(18-); In dimethyl sulfoxide; at 70 ℃; for 24h;

DOI:10.1021/acscatal.9b03415

upstream raw materials:

N-glycylserine

N-chloroacetyl-DL-serine

Gly-Ser

O-(tert-butyl)-L-serylglycine

Refernces

• 1、 Conic, Dragan,De Azambuja, Francisco,Harvey, Jeremy N.,Loosen, Alexandra,Parac-Vogt, Tatjana N.,Van Den Besselaar, Maxime. "En Route to a Heterogeneous Catalytic Direct Peptide Bond Formation by Zr-Based Metal-Organic Framework Catalysts". . p. 7647 - 7658. Retrieved 2021/06/30.
• 2、 De Azambuja, Francisco,Parac-Vogt, Tatjana N.. "Water-Tolerant and Atom Economical Amide Bond Formation by Metal-Substituted Polyoxometalate Catalysts". . p. 10245 - 10252. Retrieved 2019/11/03.