(4S)-4-N-Fmoc-amino-1-Boc-L-proline

Base Information

• Chemical Name: (4S)-4-N-Fmoc-amino-1-Boc-L-proline
• CAS No.: 174148-03-9
• Molecular Formula: C25H28N2O6
• Molecular Weight: 452.507
• Hs Code.: 29242990
• European Community (EC) Number: 640-846-3
• DSSTox Substance ID: DTXSID10373257
• Nikkaji Number: J978.314H
• Wikidata: Q72449325
• Mol file: 174148-03-9.mol

Synonyms:174148-03-9;(4S)-4-N-Fmoc-amino-1-Boc-L-proline;N-Boc-cis-4-N-Fmoc-amino-L-proline;N-Boc-cis-4-Fmoc-Amino-L-proline;(2S,4S)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid;(2S,4S)-4-(((9H-fluoren-9-yl)methoxy)carbonylamino)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid;(2S,4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid;N-Boc-cis-4-(Fmoc-amino)-L-proline;(2S,4S)-1-[(TERT-BUTOXY)CARBONYL]-4-({[(9H-FLUOREN-9-YL)METHOXY]CARBONYL}AMINO)PYRROLIDINE-2-CARBOXYLIC ACID;MFCD00673782;(4S)-1-(tert-Butoxycarbonyl)-4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-L-proline;Boc-cisPro(4-NHFmoc)-OH;SCHEMBL1393299;DTXSID10373257;UPXRTVAIJMUAQR-BTYIYWSLSA-N;(2S,4S)-FMOC-4-AMINO-1-BOC-PYRROLIDINE-2-CARBOXYLIC ACID;AKOS015841279;AKOS015893097;CS-W011579;(2S,4S)-Boc-4-(Fmoc-amino)-proline;AS-38137;N-Boc-cis-4-N-Fmoc-amino-L-proline, 97%;(2S,4S)-BOC-GAMMA-(FMOC-AMINO)-PROLINE;EN300-1723865;J-010970;1-(tert-Butoxycarbonyl)-4alpha-(9H-fluoren-9-ylmethoxycarbonylamino)-L-proline;(2S,4S)-4-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER

Chemical Property of (4S)-4-N-Fmoc-amino-1-Boc-L-proline

Chemical Property:

• Appearance/Colour: White to off-white crystalline powder
• Melting Point: 150-154 °C(lit.)
• Refractive Index: 1.627
• Boiling Point: 650.2 °C at 760 mmHg
• PKA: 3.81±0.40(Predicted)
• Flash Point: 347.029 °C
• PSA: 105.17000
• Density: 1.332 g/cm³
• LogP: 4.31650
• Storage Temp.: Store at 0-5°C
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 452.19473662
• Heavy Atom Count: 33
• Complexity: 728

Purity/Quality:

99% ^*data from raw suppliers

N-?Boc-?cis-?4-?N-?Fmoc-?amino-?L-?proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(CC1C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@H](C[C@H]1C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Uses: also available as trans isomer, see 1-00972

Technology Process of (4S)-4-N-Fmoc-amino-1-Boc-L-proline

There total 9 articles about (4S)-4-N-Fmoc-amino-1-Boc-L-proline 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%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + cis-1-(1,1-dimethylethyoxycarbonyl)-4-amino-L-proline (132622-66-3) → (2S,4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (174148-03-9)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; at 20 ℃; for 5h;

Reference yield: 90.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + cis-1-(1,1-dimethylethyoxycarbonyl)-4-amino-L-proline (132622-66-3) → (2S,4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (174148-03-9)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/jm701214z

Reference yield: 58.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + (2S,4S)-4-amino-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (121148-01-4,1018667-18-9) → (2S,4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (174148-03-9)

Guidance literature:

(2S,4S)-4-amino-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester; With sodium hydrogencarbonate; In 1,4-dioxane; water; at 20 ℃; for 0.5h;

(fluorenylmethoxy)carbonyl chloride; In 1,4-dioxane; water; at 20 ℃;

DOI:10.1016/j.ejmech.2018.04.039

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

cis-1-(1,1-dimethylethyoxycarbonyl)-4-amino-L-proline

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(2S,4R)-4-(methylsulfonyloxy)pyrrolidine-1,2-dicarboxylic acid 1-tert-butylester-2-methylester

Downstream raw materials:

Ac-[γAmp(N^α-Ac)]-NH2

(2S,4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

C₄₉H₅₁BN₄O₇

Refernces

• 1、 Bhosle, Govind S.,Kharche, Shalmali,Kumar, Santosh,Sengupta, Durba,Maiti, Souvik,Fernandes, Moneesha. "Superior HIV-1 TAR Binders with Conformationally Constrained R52 Arginine Mimics in the Tat(48–57) Peptide". supporting information. p. 220 - 226. Retrieved 2018/01/22.
• 2、 Zanardi, Franca,Burreddu, Paola,Rassu, Gloria,Auzzas, Luciana,Battistini, Lucia,Curti, Claudio,Sartori, Andrea,Nicastro, Giuseppe,Menchi, Gloria,Cini, Nicoletta,Bottonocetti, Anna,Raspanti, Silvia,Casiraghi, Giovanni. "Discovery of subnanomolar arginine-glycine-aspartate-based αvβ3/αvβ5 integrin binders embedding 4-aminoproline residues". . p. 1771 - 1782. Retrieved 2008/09/21.