D-Tryptophan benzyl ester

Base Information

• Chemical Name: D-Tryptophan benzyl ester
• CAS No.: 141595-98-4
• Molecular Formula: C18H18 N2 O2
• Molecular Weight: 294.353
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID60426409
• Nikkaji Number: J1.032.436J
• Wikidata: Q82239331
• ChEMBL ID: CHEMBL188529
• Mol file: 141595-98-4.mol

Synonyms:D-Tryptophan benzyl ester;141595-98-4;benzyl (2R)-2-amino-3-(1H-indol-3-yl)propanoate;(R)-Benzyl 2-amino-3-(1H-indol-3-yl)propanoate;CHEMBL188529;D-TRYPTOPHAN BENZYL ESTER 98;H-DTrp-OBzl;2-Amino-3-(1H-indol-3-yl)-propionic acid benzyl ester;SCHEMBL8025702;D-Tryptophan benzyl ester, 98%;DTXSID60426409;TYQYRKDGHAPZRF-MRXNPFEDSA-N;BDBM50154574;CS-0201859;J-007521

Chemical Property of D-Tryptophan benzyl ester

Chemical Property:

• Vapor Pressure: 9.59E-10mmHg at 25°C
• Melting Point: 77-80 °C(lit.)
• Refractive Index: 1.659
• Boiling Point: 489.9oC at 760 mmHg
• Flash Point: 250.1oC
• PSA: 68.11000
• Density: 1.247g/cm3
• LogP: 3.48140
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 294.136827821
• Heavy Atom Count: 22
• Complexity: 368

Purity/Quality:

98% ^*data from raw suppliers

D-Tryptophan benzyl ester 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)C(CC2=CNC3=CC=CC=C32)N
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)[C@@H](CC2=CNC3=CC=CC=C32)N

Technology Process of D-Tryptophan benzyl ester

There total 17 articles about D-Tryptophan benzyl ester 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: 90.0%

L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) + benzyl alcohol (100-51-6,185532-71-2) → L-tryptophane benzyl ester (4299-69-8,141595-98-4)

Guidance literature:

With polyphosphoric acid; at 80 ℃; for 72h;

Reference yield: 89.0%

benzyl chloride (100-44-7) + D-tryptophan (153-94-6,27732-43-0,80206-30-0,27813-82-7) → D-tryptophan benzyl ester (141595-98-4)

Guidance literature:

With Iron(III) nitrate nonahydrate; ammonia; sodium; Reflux;

DOI:10.1021/ja502205q

Reference yield: 88.0%

(S)-benzyl 2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propanoate (57229-67-1) → L-tryptophane benzyl ester (4299-69-8,141595-98-4)

Guidance literature:

(S)-benzyl 2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propanoate; With trifluoroacetic acid; In methanol; dichloromethane; at 0 ℃; for 1h;

With sodium hydrogencarbonate; In dichloromethane; water;

DOI:10.1016/j.tetlet.2009.03.121

upstream raw materials:

(S)-benzyl 2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propanoate

benzyl bromide

Boc-Trp-OH

L-tryptophan benzyl ester hydrochloride

Downstream raw materials:

L-tryptophan benzyl ester p-toluenesulfonic acid salt

N-[2-chloro-9-(tetrahydropyran-2-yl)-9H-purin-6-yl]-N-cyclopropylglycyl-L-trypthophane benzyl ester

(R)-(+)-tryptophan methyl ester hydrochloride

(S)-benzyl 2-(((benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propanoate

Refernces

• 1、 -. "Indole and quinolizine - 6 - formyl - 3 - amino-glucose, its preparation, active and application (by machine translation)". Paragraph 0017; 0019; 0020. . Retrieved 2018/04/02.
• 2、 Taglang, Céline,Martínez-Prieto, Luis Miguel,Del Rosal, Iker,Maron, Laurent,Poteau, Romuald,Philippot, Karine,Chaudret, Bruno,Perato, Serge,Sam Lone, Ana?s,Puente, Céline,Dugave, Christophe,Rousseau, Bernard,Pieters, Grégory. "Enantiospecific C-H Activation Using Ruthenium Nanocatalysts". supporting information. p. 10474 - 10477. Retrieved 2015/09/02.