Fmoc-Dab(Boc)-OH

Base Information

• Chemical Name: Fmoc-Dab(Boc)-OH
• CAS No.: 125238-99-5
• Molecular Formula: C24H28N2O6
• Molecular Weight: 440.496
• Hs Code.: 2924 29 70
• European Community (EC) Number: 834-533-2
• DSSTox Substance ID: DTXSID50373236
• Nikkaji Number: J2.017.665B
• Wikidata: Q72478121
• Mol file: 125238-99-5.mol

Synonyms:Fmoc-Dab(Boc)-OH;125238-99-5;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-((tert-butoxycarbonyl)amino)butanoic acid;Fmoc-L-dab(Boc)-OH;Fmoc-N4-Boc- L-2,4-diaminobutyric acid;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid;MFCD00151941;(2S)-4-{[(tert-butoxy)carbonyl]amino}-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)butanoic acid;N-Fmoc-N'-Boc-L-2,4-diaminobutyric acid;Fmoc-Dab(Boc);Nalpha-Fmoc-Ngamma-Boc-L-2,4-diaminobutyric acid;Fmoc-(N-gamma-Boc)-L-alpha,gamma-diaminobutyric acid;SCHEMBL4612512;SCHEMBL14039221;DTXSID50373236;LIWKOFAHRLBNMG-FQEVSTJZSA-N;BCP11624;AKOS015892812;AM10104;CS-W008024;AC-23762;DS-13304;Fmoc-Dab(Boc)-OH, >=97.0% (HPLC);F12313;(S)-N2-Fmoc-N4-Boc-2,4-diaminobutanoic acid;EN300-6487350;J-005208;Fmoc-(N-gamma-Boc)-L-alpha,gamma-diamino-butyric acid;(2S)-2-(9H-Fluorene-9-ylmethoxycarbonylamino)-4-(tert-butoxycarbonylamino)butanoic acid;(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(tert-butoxycarbonylamino)butanoic acid;(S)-4-tert-Butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid;(S)-4-tert-Butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid;N-2-(9-Fluorenylmethoxycarbonyl)-n-4-t-butoxycarbonyl-l-2,4-diaminobutyric acid;N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-gamma-t-butyloxycarbonyl-L-2,4-diaminobutyric acid;(S)-4-[(tert-Butoxycarbonyl)amino]-2-[[[(9H-fluoren-9-yl)methoxy]carbonyl]amino]butanoic acid;Butanoic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-, (2S)-

Chemical Property of Fmoc-Dab(Boc)-OH

Chemical Property:

• Vapor Pressure: 6.47E-19mmHg at 25°C
• Melting Point: 111-113℃
• Refractive Index: 1.575
• Boiling Point: 670.9 °C at 760 mmHg
• PKA: 3.79±0.10(Predicted)
• Flash Point: 359.6 °C
• PSA: 113.96000
• Density: 1.243 g/cm³
• LogP: 4.67490
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Slightly soluble in water.
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 440.19473662
• Heavy Atom Count: 32
• Complexity: 654

Purity/Quality:

≥98%,≥99%, ^*data from raw suppliers

Fmoc-Dab(Boc)-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CC(C)(C)OC(=O)NCC[C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: Fmoc-Dab(Boc)-OH,

Technology Process of Fmoc-Dab(Boc)-OH

There total 7 articles about Fmoc-Dab(Boc)-OH 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: 86.62%

di-tert-butyl dicarbonate (24424-99-5) + Nα-(9-fluorenylmethoxycarbonyl)-L-2,4-diaminobutyric acid (161420-87-7,201484-12-0) → (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid (125238-99-5,114360-56-4)

Guidance literature:

With sodium hydroxide; In water; acetone; at 0 - 10 ℃; for 4h; pH=7.5 - 8; pH-value;

Reference yield: 73.0%

(S)-(3-fluoren-9-yl-9-methoxycarbonyl)-4-[2-(tert-butyloxycarbonylamino)ethyl]-5-oxazolidinone → (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid (125238-99-5,114360-56-4)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 20 ℃;

DOI:10.1080/00397910600772827

Reference yield:

N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine (71989-20-3) → (S)-4-tert-butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)butyric acid (125238-99-5,114360-56-4)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine; bis-[(trifluoroacetoxy)iodo]benzene / 1.) CH₃CN, H₂O, 60 deg C, 2.) CH₃CN, H₂O, 60 deg C, 5 h

2: sodium hydrogencarbonate / water; acetonitrile / 6 h

With pyridine; sodium hydrogencarbonate; bis-[(trifluoroacetoxy)iodo]benzene; In water; acetonitrile;

DOI:10.1016/0223-5234(96)88216-X

upstream raw materials:

di-tert-butyl dicarbonate

N_α-(9-fluorenylmethoxycarbonyl)-L-2,4-diaminobutyric acid

9H-9-fluorenylmethyl (4S)-4-(3-azido-2-oxopropyl)-5-oxo-1,3-oxazolone-3-carboxylate

N^α-Fmoc-Glu-5-oxazolidinone

Downstream raw materials:

Fmoc-L-Dab(Boc)-OBn

(1'S, 2S)-4-(N-Boc-amino)-N'-(1'-carbamoyl-2'-phenylethyl)-2-(N''-Fmoc-amino)butanamide

4-(N-Boc-amino)-N'-2-(3-chlorophenyl)ethyl-(S)-2-(N''-Fmoc-amino)butanamide

(S)-9-fluorenylmethyl 10-(2,2-diphenylethyl)-2,2-dimethyl-18-phenyl-4,9,13,16-tetraoxo-3,17-dioxa-5,10,15-triazaoctadecan-8-ylcarbamate

Refernces

• 1、 -. "A Nα-fluorenylmethyloxycarbonyl-Nγ-tert-butoxy carbonyl-L-2,4-diamino-butyric acid synthetic method (by machine translation)". Paragraph 0020. . Retrieved 2016/10/09.
• 2、 Sakura, Naoki,Itoh, Tatsuya,Uchida, Yoshiki,Ohki, Kazuhiro,Okimura, Keiko,Chiba, Kenzo,Sato, Yuki,Sawanishi, Hiroyuki. "The contribution of the N-terminal structure of polymyxin B peptides to antimicrobial and lipopolysaccharide binding activity". . p. 1915 - 1924. Retrieved 2007/10/03.