Fmoc-D-Phe(4-NHBoc)-OH

Base Information

• Chemical Name: Fmoc-D-Phe(4-NHBoc)-OH
• CAS No.: 214750-77-3
• Molecular Formula: C₂₉H₃₀N₂O₆
• Molecular Weight: 502.567
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID60427335
• Wikidata: Q72478113
• Mol file: 214750-77-3.mol

Synonyms:214750-77-3;Fmoc-D-Phe(4-NHBoc)-OH;Fmoc-4-(Boc-amino)-D-phenylalanine;(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]propanoic acid;Fmoc-D-4-aminophe(Boc);4-(Boc-amino)-N-Fmoc-D-phenylalanine;Fmoc-p-amino-Phe(Boc)-OH;boc-d-phe(4-nhboc)-oh;SCHEMBL14039181;DTXSID60427335;MFCD00798642;AKOS015837396;AKOS015895488;AC-9630;PS-12143;CS-0154414;A50172;Fmoc-4-(Boc-amino)-D-phenylalanine, AldrichCPR;Fmoc-D-4-Aminophenylalanine(Boc) (Fmoc-D-Phe(4-NHBoc)-OH);(R)-3-(4-tert-Butoxycarbonylamino-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid

Chemical Property of Fmoc-D-Phe(4-NHBoc)-OH

Chemical Property:

• Vapor Pressure: 6.37E-19mmHg at 25°C
• Refractive Index: 1.622
• Boiling Point: 671.037 °C at 760 mmHg
• PKA: 3.80±0.10(Predicted)
• Flash Point: 359.631 °C
• PSA: 113.96000
• Density: 1.281 g/cm³
• LogP: 6.03190
• Storage Temp.: -15°C
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 502.21038668
• Heavy Atom Count: 37
• Complexity: 781

Purity/Quality:

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

Fmoc-4-(Boc-amino)-D-phenylalanine ^*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)NC1=CC=C(C=C1)CC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Isomeric SMILES: CC(C)(C)OC(=O)NC1=CC=C(C=C1)C[C@H](C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Uses: Fmoc-4-(Boc-amino)-D-phenylalanine is an intermediate used to prepare doxorubicin-formaldehyde peptide conjugates targeting αvβ3 integrin. It is also used in the synthesis of peptide acyloxymethyl ketones as selective caspases inhibitors.

Technology Process of Fmoc-D-Phe(4-NHBoc)-OH

There total 2 articles about Fmoc-D-Phe(4-NHBoc)-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:

di-tert-butyl dicarbonate (24424-99-5) + 4-amino-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanine (95753-56-3,324017-21-2) → N-α-(9-fluoromethoxycarbonyl)-L-4-tert-butoxycarbonylaminophenylalanine (214750-77-3)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; water; at 0 - 20 ℃; for 14h;

DOI:10.1021/jm3016987

Reference yield:

N-α-FMOC-4-nitro-L-phenylalanine (95753-55-2,177966-63-1) → N-α-(9-fluoromethoxycarbonyl)-L-4-tert-butoxycarbonylaminophenylalanine (214750-77-3)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium 10% on activated carbon; ammonium formate / methanol / 14 h / 20 °C

2: sodium hydrogencarbonate / water; 1,4-dioxane / 14 h / 0 - 20 °C

With palladium 10% on activated carbon; ammonium formate; sodium hydrogencarbonate; In 1,4-dioxane; methanol; water;

DOI:10.1021/jm3016987

Reference yield: 87.28%

methylamine hydrochloride (593-51-1) + N-α-(9-fluoromethoxycarbonyl)-L-4-tert-butoxycarbonylaminophenylalanine (214750-77-3) → C30H33N3O5

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 ℃; for 1h;

upstream raw materials:

N-α-FMOC-4-nitro-L-phenylalanine

di-tert-butyl dicarbonate

4-amino-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanine

Refernces