(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-phenylpentanoic acid

Base Information

• Chemical Name: (S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-phenylpentanoic acid
• CAS No.: 219967-74-5
• Molecular Formula: C26H25NO4
• Molecular Weight: 415.48
• Hs Code.: 2924299090
• European Community (EC) Number: 838-429-8
• Nikkaji Number: J3.656.326E
• Mol file: 219967-74-5.mol

Synonyms:219967-74-5;(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-phenylpentanoic acid;Fmoc-(S)-3-Amino-5-phenylpentanoic acid;(3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-5-phenylpentanoic acid;Fmoc-(S)-3-Amino-5-phenyl-pentanoic acid;Fmoc-(S)- 3-Amino-5-phenyl-pentanoic acid;(S)-3-(Fmoc-amino)-5-phenylpentanoic acid;Fmoc-beta-Nva(5-phenyl)-OH;SCHEMBL14332393;FYJRCXFXXJMPFO-IBGZPJMESA-N;MFCD01861029;AKOS015912024;AM84298;AC-22145;PS-12269;CS-0062188;J3.656.326E;EN300-816480;(3S)-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-5-phenylpentanoic acid;(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-phenylpentanoicacid;(S)-3-[(9H-Fluorene-9-ylmethoxycarbonyl)amino]-5-phenylpentanoic acid;Benzenepentanoic acid, -[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-, (S)-

Chemical Property of (S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-phenylpentanoic acid

Chemical Property:

• Vapor Pressure: 3.47E-18mmHg at 25°C
• Melting Point: 176-177 °C
• Refractive Index: 1.616
• Boiling Point: 657.5 °C at 760 mmHg
• PKA: 4.36±0.10(Predicted)
• Flash Point: 351.5 °C
• PSA: 75.63000
• Density: 1.234 g/cm³
• LogP: 5.39210
• Storage Temp.: 2-8°C
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 415.17835828
• Heavy Atom Count: 31
• Complexity: 580

Purity/Quality:

98%min ^*data from raw suppliers

Fmoc-(S)-3-amino-5-phenylpentanoicAcid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CCC(CC(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Isomeric SMILES: C1=CC=C(C=C1)CC[C@@H](CC(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Uses: Fmoc-(S)-3-amino-5-phenylpentanoic Acid is an intermediate used in the synthesis of chemical modulators of heat shock protein 70 (Hsp70). It is also used to prepare guanidinoglycosides with inventive use of Mitsunobu conditions and diazabicycloundecene.

Technology Process of (S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-phenylpentanoic acid

There total 4 articles about (S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-phenylpentanoic acid 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: 64.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (S)-3-Amino-5-phenyl-pentanoic acid; compound with trifluoro-acetic acid → (S)-3-(<<(9H-fluoren-9-yl)methoxy>carbonyl>amino)-5-phenylpentanoic acid (219967-74-5)

Guidance literature:

With sodium carbonate; In acetone; for 2h;

DOI:10.1002/(SICI)1522-2675(19981216)81:12<2141::AID-HLCA2141>3.0.CO;2-5

Reference yield:

Boc-L-homophenylalanine (82732-07-8,108524-68-1,142926-43-0,100564-78-1) → (S)-3-(<<(9H-fluoren-9-yl)methoxy>carbonyl>amino)-5-phenylpentanoic acid (219967-74-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) i-BuOCOCl, N-methylmorpholine / 1.) THF, -20 deg C, 20 min; 2.) THF, Et₂O, -5 deg C to RT, 4 h

2: 66 percent / H₂O, CF₃COOAg / tetrahydrofuran; triethylamine / -25 deg C to RT, 4-5 h

3: 440 mg / 1 h / Ambient temperature

4: 64 percent / aq. Na₂CO₃ / acetone / 2 h

With 4-methyl-morpholine; water; silver trifluoroacetate; sodium carbonate; isobutyl chloroformate; In tetrahydrofuran; triethylamine; acetone;

DOI:10.1002/(SICI)1522-2675(19981216)81:12<2141::AID-HLCA2141>3.0.CO;2-5

Reference yield:

(S)-3-<<(tert-butoxy)carbonyl>amino>-5-phenylpentanoic acid (218608-84-5,955314-80-4) → (S)-3-(<<(9H-fluoren-9-yl)methoxy>carbonyl>amino)-5-phenylpentanoic acid (219967-74-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 440 mg / 1 h / Ambient temperature

2: 64 percent / aq. Na₂CO₃ / acetone / 2 h

With sodium carbonate; In acetone;

DOI:10.1002/(SICI)1522-2675(19981216)81:12<2141::AID-HLCA2141>3.0.CO;2-5

upstream raw materials:

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

Boc-L-homophenylalanine

(S)-3-<<(tert-butoxy)carbonyl>amino>-5-phenylpentanoic acid

(S)-3-(<(tert-butoxy)carbonyl>amino)-1-diazo-5-phenylpentan-2-one

Downstream raw materials:

3-((3S)-3-(4-(4-(4-bromophenyl)-5-(ethoxycarbonyl)-6-methyl-2-oxo-3,4-dihydropyrimidin-1(2H)-yl)butanamido)-5-phenylpentanamido)propanoic acid

(S)-N-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-N'-[2-(9-fluorenylmethoxycarbonyl)amino-4-phenylbutylcarbonyl]methylisothiourea

Refernces