Fmoc-D-Trp-OH

Base Information

• Chemical Name: Fmoc-D-Trp-OH
• CAS No.: 86123-11-7
• Molecular Formula: C₂₆H₂₂N₂O₄
• Molecular Weight: 426.472
• Hs Code.: 29339900
• European Community (EC) Number: 630-404-8
• Nikkaji Number: J577.228A
• Wikidata: Q106902920
• ChEMBL ID: CHEMBL303800
• Mol file: 86123-11-7.mol

Synonyms:Fmoc-D-Trp-OH;86123-11-7;Fmoc-D-tryptophan;(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(1H-indol-3-yl)propanoic acid;N-A-FMOC-D-TRYPTOPHAN;CHEMBL303800;D-Tryptophan, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-;MFCD00062954;N-(9-fluorenylmethoxycarbonyl)-D-tryptophan;Nalpha-[(9H-Fluoren-9-ylmethoxy)carbonyl]-D-tryptophan;Nalpha-Fmoc-D-tryptophan;N-|A-Fmoc-D-tryptophan;Fmoc-D-Trp-OH, 98%;SCHEMBL119594;MGHMWKZOLAAOTD-XMMPIXPASA-N;Fmoc-D-Trp-OH, >=98.0%;BDBM50043808;AKOS015922809;AM82280;CS-W009679;AC-24063;AS-12715;F0609;Na-(9-Fluorenylmethoxycarbonyl)-D-tryptophan;EN300-81265;M03377;Nalpha-(9-Fluorenylmethoxycarbonyl)-D-tryptophan;(((9H-Fluoren-9-yl)methoxy)carbonyl)-D-tryptophan;J-300268;Q-101609;(2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(1H-indol-3-yl)propanoic acid;(R)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-3-(1H-INDOL-3-YL)PROPANOIC ACID;(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(1H-indol-3-yl)-propionic acid

Chemical Property of Fmoc-D-Trp-OH

Chemical Property:

• Appearance/Colour: beige powder
• Vapor Pressure: 2.87E-21mmHg at 25°C
• Melting Point: 182-185 °C(lit.)
• Refractive Index: 29 ° (C=1, DMF)
• Boiling Point: 711.9 °C at 760 mmHg
• PKA: 3.89±0.10(Predicted)
• Flash Point: 384.3 °C
• PSA: 91.42000
• Density: 1.35 g/cm³
• LogP: 5.09320
• Storage Temp.: 2-8°C
• Solubility.: soluble in Methanol
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 426.15795719
• Heavy Atom Count: 32
• Complexity: 663

Purity/Quality:

99% ^*data from raw suppliers

Na-Fmoc-D-tryptophan 98+% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CNC5=CC=CC=C54)C(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@H](CC4=CNC5=CC=CC=C54)C(=O)O
• Uses: Nα-Fmoc-D-tryptophan is an N-Fmoc-protected form of D-Tryptophan (T947205). D-Tryptophan is an unnatural isomer of L-Tryptophan (T947210) and is classified as an essential amino acid. D-Tryptophan has been synthesized as part of some potent Oxytocin (Acetate: O878500) antagonists that treat preterm labour.

Technology Process of Fmoc-D-Trp-OH

There total 2 articles about Fmoc-D-Trp-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:

Fmoc-L-tryptophan → Fmoc-Trp-OH (35737-15-6) + N-(9-fluorenylmethoxycarbonyl)-D-tryptophan (35737-15-6,144701-22-4,86123-11-7)

Guidance literature:

With chiral column based on 3,5-dimethylphenylcarbamoylated β-cyclodextrin combining cinchona alkaloid immobilized on silica gel; In methanol; formic acid; triethylamine; acetonitrile; at 25 ℃; Reagent/catalyst; enantioselective reaction; Resolution of racemate;

DOI:10.1002/chir.23237

Reference yield:

→ N-(9-fluorenylmethoxycarbonyl)-D-tryptophan (35737-15-6,144701-22-4,86123-11-7)

Guidance literature:

Reference yield: 12.0%

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3,136132-75-7) + (4R,5S)-3-(((9H-fluoren-9-yl)methoxy)carbonyl)-5-isopropyl-2,2-dimethyloxazolidine-4-carboxylic acid + (4S,5S)-3-(((9H-fluoren-9-yl)methoxy)carbonyl)-2,2-dimethyl-5-phenyloxazolidine-4-carboxylic acid + (4S,5S)-3-(((9H-fluoren-9-yl)methoxy)carbonyl)-5-(4-methoxyphenyl)-2,2-dimethyloxazolidine-4-carboxylic acid + (E)-3-(2-((Z)-prop-1-en-1-yl)phenyl)acrylic acid + Fmoc-Pro-OH (71989-31-6) + N-(9-fluorenylmethoxycarbonyl)-D-leucine (35661-60-0,126727-03-5,114360-54-2) + Fmoc-Thr-OH (73731-37-0) + N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5) + N-(9-fluorenylmethoxycarbonyl)-D-tryptophan (35737-15-6,144701-22-4,86123-11-7) + Fmoc-Asp(Pip)-OH (200336-86-3) → C75H97N13O20

Guidance literature:

N-(9-fluorenylmethoxycarbonyl)-D-tryptophan; With 4-methyl-morpholine; ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V); In N,N-dimethyl-formamide; at 22 ℃; for 16h; Inert atmosphere;

With piperidine; In N,N-dimethyl-formamide; Inert atmosphere;

N-(fluoren-9-ylmethoxycarbonyl)glycine; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; (4R,5S)-3-(((9H-fluoren-9-yl)methoxy)carbonyl)-5-isopropyl-2,2-dimethyloxazolidine-4-carboxylic acid; (4S,5S)-3-(((9H-fluoren-9-yl)methoxy)carbonyl)-2,2-dimethyl-5-phenyloxazolidine-4-carboxylic acid; (4S,5S)-3-(((9H-fluoren-9-yl)methoxy)carbonyl)-5-(4-methoxyphenyl)-2,2-dimethyloxazolidine-4-carboxylic acid; (E)-3-(2-((Z)-prop-1-en-1-yl)phenyl)acrylic acid; Fmoc-Pro-OH; N-(9-fluorenylmethoxycarbonyl)-D-leucine; Fmoc-Thr-OH; N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine; Fmoc-Asp(Pip)-OH; Further stages;

DOI:10.1002/chem.201704277

Downstream raw materials:

9H-fluoren-9-ylmethyl -3-(1H-indol-3-ylmethyl)-4,9-dioxo-7,11-diphenyl-10-oxa-2,5,8-triazaundecanoate

(R)-3-[(R)-2-Amino-3-(1H-indol-3-yl)-propionylamino]-N-{(S)-1-[(R)-1-((S)-1-hydrazinocarbonyl-3-methyl-butylcarbamoyl)-2-methyl-propylcarbamoyl]-3-methyl-butyl}-succinamic acid tert-butyl ester

(R)-3-[(R)-2-Amino-3-(1H-indol-3-yl)-propionylamino]-4-{(S)-2-[(R)-1-((S)-1-hydrazinocarbonyl-butylcarbamoyl)-2-methyl-propylcarbamoyl]-pyrrolidin-1-yl}-4-oxo-butyric acid tert-butyl ester

(R)-3-[(R)-2-Amino-3-(1H-indol-3-yl)-propionylamino]-N-{(S)-1-[(R)-1-((S)-1-hydrazinocarbonyl-3-methyl-butylcarbamoyl)-2-methyl-propylcarbamoyl]-2-methyl-propyl}-succinamic acid tert-butyl ester

Refernces

• 1、 -. "Angiopeptin cyclopeptide compounds". . . Retrieved 2008/06/13.