D-Tryptophan, N-methyl-, methyl ester

Base Information

• Chemical Name: D-Tryptophan, N-methyl-, methyl ester
• CAS No.: 131831-87-3
• Molecular Formula: C₁₃H₁₆N₂O₂
• Molecular Weight: 232.282
• Mol file: 131831-87-3.mol

Synonyms:N-Me-D-Trp-OMe;

Chemical Property of D-Tryptophan, N-methyl-, methyl ester

Chemical Property:

• PSA: 54.12000
• LogP: 1.86230

Purity/Quality:

99.0%min ^*data from raw suppliers

N-Methyl-D-tryptophanMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-Methyl-D-tryptophan Methyl Ester is an intermediate in the synthesis of Jasplakinolide (J210700), an potent inhibitor of prostrate and breast carcinoma cell proliferation.

Technology Process of D-Tryptophan, N-methyl-, methyl ester

There total 6 articles about D-Tryptophan, N-methyl-, methyl 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: 99.0%

(R)-methyl 2-(benzyl(methyl)amino)-3-(1H-indol-3-yl)propanoate → N-methyl-(R)-tryptophan methyl ester (131831-87-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 1h; under 2068.65 Torr; Inert atmosphere;

DOI:10.1002/ejoc.201403577

Reference yield: 68.0%

methyl (R)-3-(1H-indol-3-yl)-2-(N-tert-butoxycarbonyl-N-methylamino)propanoate (122747-97-1) → N-methyl-(R)-tryptophan methyl ester (131831-87-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 23 ℃; for 1h;

DOI:10.1002/chem.200500319

Reference yield: 61.0%

D-N-formyl tryptophan methyl ester (134781-88-7) → N-methyl-(R)-tryptophan methyl ester (131831-87-3)

Guidance literature:

With dimethylsulfide borane complex; In tetrahydrofuran; 1.) 0 deg C, then r.t., 3 h, 2.) MeOH, r.t., overnight, 3.) HCl/MeOH, reflux, 1 h;

DOI:10.1021/jo00017a037

upstream raw materials:

D-N-formyl tryptophan methyl ester

formyl acetic anhydride

D-Tryptophan methyl ester

methyl (R)-3-(1H-indol-3-yl)-2-(N-tert-butoxycarbonyl-N-methylamino)propanoate

Downstream raw materials:

(E)-(2S,6R,8S)-8-<(tert-Butyldimethylsilyl)oxy>-2,4,6-trimethyl-4-nonenoyl-(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-methyl-(R)-β-tyrosine Methyl Ester

jaspamide Z₁

(R)-3-[(R)-2-[((S)-2-Amino-propionyl)-methyl-amino]-3-(2-bromo-1H-indol-3-yl)-propionylamino]-3-(4-methoxy-phenyl)-propionic acid methyl ester

N-Boc-(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-methyl-(R)-β-tyrosine Methyl Ester

Refernces

• 1、 -. "NOVEL CHONDRAMIDE DERIVATIVES". . . Retrieved 2015/11/17.
• 2、 Marimganti, Srinivasa,Yasmeen, Shazia,Fischer, Daniela,Maier, Martin E.. "Synthesis of jasplakinolide analogues containing a novel ω-amino acid". . p. 6687 - 6700. Retrieved 2007/10/03.