4-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoic acid

Base Information

• Chemical Name: 4-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoic acid
• CAS No.: 71989-16-7
• Molecular Formula: C19H18N2O5
• Molecular Weight: 354.362
• Hs Code.: 2924 29 70
• NSC Number: 334297
• Mol file: 71989-16-7.mol

Synonyms:157355-73-2;N-alpha-Fmoc-L-asparagine;N2-((9H-Fluoren-9-ylmethoxy)carbonyl)-L-asparagine;3-Carbamoyl-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoic acid;Fmoc-DL-asparagine;MFCD00037132;MFCD00062956;NSC334297;SCHEMBL2309917;EINECS 276-252-2;4-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoic acid;AKOS009158868;AB01602;AB02463;NSC 334297;NSC-334297;SY032201;SY042589;FT-0629917;FT-0629927;FT-0686516;EN300-649778;2-(Hydroxy(4-phenylbutan-2-yl)phosphoryl)acetic acid;3-Carbamoyl-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoicacid

Chemical Property of 4-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 2.43E-19mmHg at 25°C
• Melting Point: 190 °C (dec.)(lit.)
• Refractive Index: -13 ° (C=1, DMF)
• Boiling Point: 678.6 °C at 760 mmHg
• PKA: 3.68±0.10(Predicted)
• Flash Point: 364.2 °C
• PSA: 118.72000
• Density: 1.362 g/cm³
• LogP: 2.94490
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 354.12157168
• Heavy Atom Count: 26
• Complexity: 530

Purity/Quality:

99% ^*data from raw suppliers

Nα-Fmoc-L-asparagine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37/39-27-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC(=O)N)C(=O)O
• Uses: Nα-Fmoc-L-asparagine is an N-Fmoc-protected form of L-Asparagine (A790005). L-Asparagine was first isolated by Robiquet and Vauquelin from asparagus juice (a high source of L-asparagine). L-Asparagine is often incorporated into proteins, and is a basis for some cancer therapies as certain cancerous cells require L-asparagine for growth.

Technology Process of 4-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoic acid

There total 8 articles about 4-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoic 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: 87.0%

L-asparagine (70-47-3,28088-48-4,7006-34-0) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → Fmoc-Asn-OH (71989-16-7)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃;

DOI:10.1002/psc.2968

Reference yield: 83.0%

L-asparagine (70-47-3,28088-48-4,7006-34-0) + (9-fluorenyl)methyl pentafluorophenyl carbonate (88744-04-1) → Fmoc-Asn-OH (71989-16-7)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone; Ambient temperature;

Reference yield:

L-asparagine (70-47-3,28088-48-4,7006-34-0) + (9H-fluoren-9-yl)methyl azidoformate (28920-44-7) → Fmoc-Asn-OH (71989-16-7)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 20 ℃; for 48h;

DOI:10.1021/op049917z

upstream raw materials:

L-asparagine

(9-fluorenyl)methyl pentafluorophenyl carbonate

L-Asn(Trt)

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

Downstream raw materials:

N^α-fluorenylmethoxycarbonyl-L-asparagine p-nitrophenyl ester

{5-[(S)-3-Carbamoyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-pentyl}-carbamic acid tert-butyl ester

(S)-N^α-(Fluoren-9-ylmethoxycarbonyl)asparagine 4-methoxybenzyl ester

4-(Fmoc-asparginyloxymethyl)phenoxyacetic acid 2-phenacyl ester

Refernces

• 1、 Pícha, Jan,Budě?ínsky, Milo?,Machá?ková, Kate?ina,Collinsová, Michaela,Jirá?ek, Ji?í. "Optimized syntheses of Fmoc azido amino acids for the preparation of azidopeptides". . p. 202 - 214. Retrieved 2017/04/06.
• 2、 Zhou, Wei,Zhang, Xiao-Yan,Duan, Geng-Li. "Liquid-chromatography quantitative analysis of 20 amino acids after derivatization with FMOC-CI and its application to different origin Radix isatidis". experimental part. p. 509 - 515. Retrieved 2012/01/04.