N-Cbz-D-Tryptophan

Base Information

• Chemical Name: N-Cbz-D-Tryptophan
• CAS No.: 2279-15-4
• Molecular Formula: C19H18N2O4
• Molecular Weight: 338.363
• Hs Code.: 29339900
• DSSTox Substance ID: DTXSID701297570
• Nikkaji Number: J253.119D
• ChEMBL ID: CHEMBL65134
• Mol file: 2279-15-4.mol

Synonyms:Tryptophan,N-carboxy-, N-benzyl ester, D- (8CI);(2R)-2-(Benzyloxycarbonylamino)-3-(1H-indol-3-yl)propionic acid;(R)-2-(((Benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propanoicacid;Cbz-D-tryptophan;D-(Carbobenzyloxy)tryptophan;N-(Benzyloxycarbonyl)-D-tryptophan;

Chemical Property of N-Cbz-D-Tryptophan

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 3.46E-16mmHg at 25°C
• Melting Point: 122-124 °C
• Refractive Index: 11 ° (C=1, MeOH)
• Boiling Point: 619.1 °C at 760 mmHg
• PKA: 3.98±0.10(Predicted)
• Flash Point: 328.2 °C
• PSA: 91.42000
• Density: 1.341 g/cm³
• LogP: 3.48090
• Storage Temp.: Store at RT.
• Solubility.: soluble in Methanol
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 338.12665706
• Heavy Atom Count: 25
• Complexity: 464

Purity/Quality:

99% ^*data from raw suppliers

Z-D-Trp-OH ^*data from reagent suppliers

Safty Information:

• Statements: 22/22-36/37/38
• Safety Statements: 22-24/25-44-35-28-7-4

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC(CC2=CNC3=CC=CC=C32)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)N[C@H](CC2=CNC3=CC=CC=C32)C(=O)O
• Uses: Nα-Cbz-D-tryptophan is an N-Cbz-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 N-Cbz-D-Tryptophan

There total 7 articles about N-Cbz-D-Tryptophan 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: 94.0%

benzyl chloroformate (501-53-1,94274-21-2) + D-tryptophan (153-94-6,27732-43-0,80206-30-0,27813-82-7) → N-(benzyloxycarbonyl)-D-tryptophan (2279-15-4)

Guidance literature:

With sodium hydrogencarbonate; potassium carbonate; In water; acetone; at 30 ℃; for 3h; pH=8 - 10; Cooling with ice;

DOI:10.1021/acs.joc.5b01161

Reference yield: 81.0%

L-tryptophan (73-22-3,6912-86-3,54-12-6,153-94-6,63148-28-7,65556-72-1,27732-43-0,80206-30-0,27813-82-7) + 3-benzyloxycarbonyl-2-oxazolone (75819-24-8) → carbobenzyloxy-L-trytophan (2279-15-4,7432-21-5,13058-16-7,94345-99-0)

Guidance literature:

With triethylamine; In water; acetone; Ambient temperature;

DOI:10.1016/S0040-4039(00)77408-9

Reference yield: 80.0%

ethanol (64-17-5) + N-[(phenylmethoxy)carbonyl]-DL-tryptophan (13058-16-7) → N-benzyloxycarbonyl-L-tryptophan ethyl ester (41844-69-3) + N-(benzyloxycarbonyl)-D-tryptophan (2279-15-4)

Guidance literature:

With citrate buffer; DL-cysteine hydrochloride; papain; at 50 ℃; for 24h;

upstream raw materials:

aniline

N-[(phenylmethoxy)carbonyl]-DL-tryptophan

benzyl chloroformate

D-tryptophan

Downstream raw materials:

N-(N^α-benzyloxycarbonyl-D-tryptophyl)-L-tyrosin-amide

D-tryptophan

(S)-1-[2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionyl]-pyrrolidine-2-carboxylic acid 4-nitro-phenyl ester

(S)-1-[2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionyl]-pyrrolidine-2-carboxylic acid 4-nitro-phenyl ester

Refernces

• 1、 Alqahtani, Norah,Porwal, Suheel K.,James, Elle D.,Bis, Dana M.,Karty, Jonathan A.,Lane, Amy L.,Viswanathan, Rajesh. "Synergism between genome sequencing, tandem mass spectrometry and bio-inspired synthesis reveals insights into nocardioazine B biogenesis". supporting information. p. 7177 - 7192. Retrieved 2015/07/01.
• 2、 Hewitt, Peter R.,Cleator, Ed,Ley, Steven V.. "A concise total synthesis of (+)-okaramine C". . p. 2415 - 2417. Retrieved 2007/10/03.