Succinimido (S)-2-[(tert-butoxycarbonyl)amino]propionate

Base Information

• Chemical Name: Succinimido (S)-2-[(tert-butoxycarbonyl)amino]propionate
• CAS No.: 3392-05-0
• Molecular Formula: C12H18N2O6
• Molecular Weight: 286.285
• Hs Code.: 29224999
• NSC Number: 334372
• Mol file: 3392-05-0.mol

Synonyms:2-tert-butoxycarbonylamino-propionic acid 2,5-dioxopyrrolidin-1-yl ester;NSC334372;SCHEMBL356359;COMUWNFVTWKSDT-UHFFFAOYSA-N;EINECS 222-229-7;NSC 334372;NSC-334372;(2,5-dioxopyrrolidin-1-yl) 2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate;Boc-L-Alanine N-hydroxysuccinimde ester;AM20090518;FT-0634824;Succinimido (S)-2-(tert-butoxycarbonyl)amino]propionate

Chemical Property of Succinimido (S)-2-[(tert-butoxycarbonyl)amino]propionate

Chemical Property:

• Melting Point: 161-163 °C
• Refractive Index: 1.51
• PKA: 10.81±0.46(Predicted)
• PSA: 102.01000
• Density: 1.27 g/cm³
• LogP: 0.83560
• Storage Temp.: −20°C
• Sensitive.: Moisture Sensitive
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 286.11648630
• Heavy Atom Count: 20
• Complexity: 424

Purity/Quality:

99% ^*data from raw suppliers

Boc-Ala-OSu ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)ON1C(=O)CCC1=O)NC(=O)OC(C)(C)C
• Uses: Reactant involved in synthesis of:Muramyldipeptide analogs via solid-phase synthesisMicrocin C analogs for use as antibacterialsLipid I and nucleoside diphosphate peptide derivatives via N-methylimidazolium chloride catalyzed couplingN-Protected dipeptide acidsFree and peptide-bound glycated amino acids for studies of interactions with human Caco-2 interstinal epithelial cell apical membrane transport proteins7-Substituted camptothecin conjugates with RGD-peptides as avβ3 integrin ligands

Technology Process of Succinimido (S)-2-[(tert-butoxycarbonyl)amino]propionate

There total 11 articles about Succinimido (S)-2-[(tert-butoxycarbonyl)amino]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: 98.0%

L-N-Boc-Ala (15761-38-3) + bis(N-hydroxysuccinimide) sulfite (90704-86-2) → Boc-Ala-O-N-hydroxysuccinimide (3392-05-0)

Guidance literature:

With pyridine; In acetonitrile; at 20 ℃; for 1.5h; further solvent, base;

DOI:10.1007/BF01141728

Reference yield: 96.7%

L-N-Boc-Ala (15761-38-3) + N-hydroxysuccinimido diphenyl phosphate (75513-55-2) → Boc-Ala-O-N-hydroxysuccinimide (3392-05-0)

Guidance literature:

DOI:10.1021/jo00136a033

Reference yield: 95.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + L-N-Boc-Ala (15761-38-3) → Boc-Ala-O-N-hydroxysuccinimide (3392-05-0)

Guidance literature:

With dicyclohexyl-carbodiimide; In 1,4-dioxane; Ambient temperature;

DOI:10.1002/jps.2600760210

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

L-N-Boc-Ala

N-hydroxysuccinimido diphenyl phosphate

1,2,2,2-tetrachloroethyl-(N-succinimidyl)carbonate

Downstream raw materials:

(S)-(-)-N-(tert-butyloxycarbonyl)-N',N'-tetramethylenealaninamide

(N-tert-butoxycarbonyl-L-alanyl)-L-valine

(S)-2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)-3-phenylpropanoic acid

Boc-Ala-Lys(Boc)-NHNH-Z

Refernces

• 1、 Zemlyakov,Kur'yanov,Tsikalova,Chirva. "Synthesis of conjugates of glyco amino acids and glycopeptides with carboxylic acid hydrazides". . p. 568 - 570. Retrieved 1997.
• 2、 Yang, Jinhua,Wang, Changliu,Xu, Silin,Zhao, Junfeng. "Ynamide-Mediated Thiopeptide Synthesis". supporting information. p. 1382 - 1386. Retrieved 2019/01/08.
• 3、 -. "CHEMICAL SYNTHESIS AND ANTI-TUMOR AND ANTI-METASTATIC EFFECTS OF DUAL FUNCTIONAL CONJUGATE". Paragraph 0137. . Retrieved 2017/10/24.