Boc-Dap(Fmoc)-OH

Base Information

• Chemical Name: Boc-Dap(Fmoc)-OH
• CAS No.: 122235-70-5
• Molecular Formula: C₂₃H₂₆N₂O₆
• Molecular Weight: 426.469
• Hs Code.: 29242990
• DSSTox Substance ID: DTXSID20427134
• Nikkaji Number: J1.401.634A
• Wikidata: Q72449335
• Mol file: 122235-70-5.mol

Synonyms:Boc-Dap(Fmoc)-OH;122235-70-5;(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)propanoic acid;(2S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;Boc-3-(Fmoc-amino)-L-alanine;MFCD00235897;(S)-2-(Boc-Amino)-3-(Fmoc-amino)propionic acid;SCHEMBL999883;DTXSID20427134;MVWPBNQGEGBGRF-IBGZPJMESA-N;AMY15581;AKOS016842389;CS-W009385;(2S)-2-(tert-butoxycarbonylamino)-3-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid;L-Alanine, N-[(1,1-Dimethylethoxy)Carbonyl]-3-[[(9H-Fluoren-9-Ylmethoxy)Carbonyl]Amino]-;Boc-3-Fmoc-L-2,3-diaminopropionic acid;DS-13301;Boc-Dap(Fmoc)-OH, >=98.0% (HPLC);EN300-650832;F16410;A804858;J-004774;(S)-2-tert- Butoxycarbonylamino-3-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid;(S)-2-tert-Butoxycarbonylamino-3-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid;(S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-(tert-butoxycarbonylamino)propanoic acid;N-[(1,1-dimethylethoxy)carbonyl]-3-[(9H-fluoren-9-ylmethoxy)carbonyl]amino-L-alanine;(2S)-2-[(tert-Butoxycarbonyl)amino]-3-[(9H-fluorene-9-yl)methoxycarbonylamino]propionic acid;(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoic acid;N-alpha-(t-Butyloxycarbonyl)-N-beta-(9-fluorenylmethyloxycarbonyl)-L-2,3-diaminopropionic acid (Boc-L-Dap(Fmoc)-OH)

Chemical Property of Boc-Dap(Fmoc)-OH

Chemical Property:

• Vapor Pressure: 6.45E-18mmHg at 25°C
• Refractive Index: 1.58
• Boiling Point: 652.5 °C at 760 mmHg
• PKA: 3?+-.0.10(Predicted)
• Flash Point: 348.4 °C
• PSA: 113.96000
• Density: 1.263 g/cm³
• LogP: 4.28480
• Storage Temp.: Store at RT.
• Solubility.: Soluble in 2ml dimethyl formamide 0.3gram.
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 426.17908655
• Heavy Atom Count: 31
• Complexity: 639

Purity/Quality:

98%,99%, ^*data from raw suppliers

Boc-dap(fmoc)-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)NC(CNC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CNC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)C(=O)O
• Uses: It has been used in the synthesis of target chelator, the tris-catechol compound 2.

Technology Process of Boc-Dap(Fmoc)-OH

There total 6 articles about Boc-Dap(Fmoc)-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: 88.0%

bis-(trifluoroacetoxy)-iodo-benzene + N-[(1,1-dimethylethoxy)carbonyl]-L-asparagine (177740-14-6) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → N-[(1,1-dimethylethoxy)carbonyl]-3-[(9H1-fluoren-9-ylmethoxy)carbonyl]amnino-L-alanine + Boc-Dap(Fmoc)-OH (131570-56-4,122235-70-5,159002-16-1)

Guidance literature:

With pyridine; sodium bicarbonate; In water; N,N-dimethyl-formamide; acetone;

Reference yield: 71.2%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (S)-3-amino-2-tert-butoxycarbonylaminopropionic acid (76387-70-7) → Boc-Dap(Fmoc)-OH (131570-56-4,122235-70-5,159002-16-1)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; water; at 20 ℃; for 2h;

DOI:10.1016/S0968-0896(98)00232-6

Reference yield:

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + (S)-3-amino-2-tert-butoxycarbonylaminopropionic acid (76387-70-7) → Boc-Dap(Fmoc)-OH (131570-56-4,122235-70-5,159002-16-1)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; 1.) 1 h, 0 deg C, 2.) 1 h, 25 deg C;

DOI:10.1021/jo00014a006

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

(S)-3-amino-2-tert-butoxycarbonylaminopropionic acid

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

N-tert-butyloxycarbonylasparagine

Downstream raw materials:

Boc-Dap(Fmoc)-Ala p-nitrobenzyl ester

Refernces

• 1、 Aiello, Donatella,Athanassopoulos, Constantinos M.,Mazzotti, Fabio,Siciliano, Carlo,Temperini, Andrea,de Luca, Pierantonio. "2,3-Diaminopropanols obtained from D-serine as intermediates in the synthesis of protected 2,3-L-diaminopropanoic acid (L-DAP) methyl esters". . . Retrieved 2020/03/23.
• 2、 Tosatti, Paolo,Horn, Joachim,Campbell, Amanda J.,House, David,Nelson, Adam,Marsden, Stephen P.. "Iridium-catalyzed asymmetric allylic amination with polar amines: Access to building blocks with lead-like molecular properties". supporting information; experimental part. p. 3153 - 3157. Retrieved 2011/03/18.