9H-fluoren-9-ylmethyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate

Base Information

• Chemical Name: 9H-fluoren-9-ylmethyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS No.: 146803-43-2
• Molecular Formula: C24H21NO3
• Molecular Weight: 371.436
• DSSTox Substance ID: DTXSID501177192
• Nikkaji Number: J971.571A
• Mol file: 146803-43-2.mol

Synonyms:146803-43-2;9H-fluoren-9-ylmethyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate;(S)-(9H-Fluoren-9-yl)methyl (1-oxo-3-phenylpropan-2-yl)carbamate;Fmoc-Phe Wang resin;SCHEMBL3039215;AAAFQLPJNOITCL-SFHVURJKSA-N;DTXSID501177192;MFCD01318543;AKOS022168264;(S)-3-Phenyl-2-(Fmoc-amino)propanal;MH-0723;CS-0376034;M03483;Fmoc-L-phenylalanine Sasrin(R) resin ester, 200-400 mesh;Fmoc-Phe-Wang resin, 100-200 mesh 0.792mmol/gm 1% DVB;(S)-(9H-Fluoren-9-yl)methyl(1-oxo-3-phenylpropan-2-yl)carbamate;9H-Fluoren-9-ylmethyl N-[(1S)-1-formyl-2-phenylethyl]carbamate;Fmoc-Phe-Wang resin, extent of labeling: 0.4-0.8 mmol/g loading;(9H-fluoren-9-yl)methyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate

Chemical Property of 9H-fluoren-9-ylmethyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate

Chemical Property:

• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 371.15214353
• Heavy Atom Count: 28
• Complexity: 508

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(C=O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](C=O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Technology Process of 9H-fluoren-9-ylmethyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate

There total 13 articles about 9H-fluoren-9-ylmethyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate 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: 92.0%

(9H-fluoren-9-yl)methyl (S)-(1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (299207-24-2) → Fmoc-Phe-H (146803-43-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1016/S0957-4166(98)00183-9

Reference yield: 88.0%

(9-fluorenylmethoxycarbonyl)-L-phenylalaninol (129397-83-7) → Fmoc-Phe-H (146803-43-2)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; ethyl acetate; at 80 ℃; for 1h;

DOI:10.1080/00397910701555469

Reference yield: 83.0%

Fmoc-L-phenylalanine ethanethiol ester (459142-81-5) → Fmoc-Phe-H (146803-43-2)

Guidance literature:

With triethylsilane; palladium on activated charcoal; In acetone; at 20 ℃;

DOI:10.1055/s-2002-31969

upstream raw materials:

N-(fluorenylmethyloxycarbonyl)-L-phenylalanine S-benzyl thioester

2S-flouren-9-ylmethoxycarbonylamino-3-phenylpropionyl chloride

(9H-fluoren-9-yl)methyl (S)-(1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

(9-fluorenylmethoxycarbonyl)-L-phenylalaninol

Downstream raw materials:

(1-benzyl-2,2-dimethoxy-ethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester

2-amino-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-phenyl-thiobutyric acid S-p-tolyl ester

(1-benzyl-3-nitro-3-p-tolylsulfanyl-allyl)-carbamic acid 9H-fluoren-9-ylmethyl ester

2-tert-butoxycarbonylamino-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-phenyl-thiobutyric acid S-p-tolyl ester

Refernces

• 1、 González-Gómez, José C.,Uriarte-Villares, Eugenio,Figueroa-Pérez. "A cyclative cleavage approach to the solid phase synthesis of 2-oxo-1,4-piperazines". . p. 1085 - 1088. Retrieved 2002.
• 2、 Sang, Peng,Shi, Yan,Lu, Junhao,Chen, Lihong,Yang, Leixiang,Borcherds, Wade,Abdulkadir, Sami,Li, Qi,Daughdrill, Gary,Chen, Jiandong,Cai, Jianfeng. "α-Helix-Mimicking Sulfono-γ-AApeptide Inhibitors for p53-MDM2/MDMX Protein-Protein Interactions". supporting information. p. 975 - 986. Retrieved 2020/03/10.
• 3、 Pacifico, Salvatore,Ferretti, Valeria,Albanese, Valentina,Fantinati, Anna,Gallerani, Eleonora,Nicoli, Francesco,Gavioli, Riccardo,Zamberlan, Francesco,Preti, Delia,Marastoni, Mauro. "Synthesis and biological activity of peptide α-ketoamide derivatives as proteasome inhibitors". supporting information. p. 1086 - 1092. Retrieved 2019/08/01.