tri-tert-butyl N--L-glutamate

Base Information

• Chemical Name: tri-tert-butyl N--L-glutamate
• CAS No.: 32719-56-5
• Molecular Formula: C₃₀H₄₆N₂O₉
• Molecular Weight: 578.703
• Mol file: 32719-56-5.mol

Synonyms:tri-tert-butyl N--L-glutamate

Chemical Property of tri-tert-butyl N--L-glutamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tri-tert-butyl N--L-glutamate

There total 4 articles about tri-tert-butyl N--L-glutamate 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: 81.8%

(S)-2-(benzyloxycarbonylamino)pentanedioic acid tert-butyl ester (5891-45-2) + L-glutamic acid di-tert-butyl ester hydrochloride (32677-01-3) → tri-tert-butyl N--L-glutamate (32719-56-5)

Guidance literature:

(S)-2-(benzyloxycarbonylamino)pentanedioic acid tert-butyl ester; With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 10 - 20 ℃; for 0.5h; Large scale;

L-glutamic acid di-tert-butyl ester hydrochloride; In dichloromethane; at 20 ℃; for 20h; Large scale;

Reference yield: 77.0%

L-glutamic acid di-tert-butyl ester hydrochloride (32677-01-3) + N-(benzyloxycarbonyl)-L-glutamic acid α-t-butyl ester dicyclohexylamine salt (34897-61-5) → tri-tert-butyl N--L-glutamate (32719-56-5)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; for 17h;

DOI:10.1002/jhet.5570270654

Reference yield:

di-tert-butyl N-Cbz-L-glutamate (16881-41-7) → tri-tert-butyl N--L-glutamate (32719-56-5)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 10percent Pd/C / methanol; acetic acid

2: (PhO)2P(=O)N₃

With diphenyl phosphoryl azide; hydrogen; palladium on activated charcoal; In methanol; acetic acid;

DOI:10.1021/jo00010a038

upstream raw materials:

di-tert-butyl L-glutamate

(S)-2-(benzyloxycarbonylamino)pentanedioic acid tert-butyl ester

L-glutamic acid di-tert-butyl ester hydrochloride

N-(benzyloxycarbonyl)-L-glutamic acid α-t-butyl ester dicyclohexylamine salt

Downstream raw materials:

(S)-2-((S)-4-Carboxy-4-{2-fluoro-4-[(4-hydroxy-2-methyl-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-pentanedioic acid; compound with trifluoro-acetic acid

(S)-2-((S)-4-Carboxy-4-{4-[(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-pentanedioic acid; compound with trifluoro-acetic acid

(S)-2-((S)-4-tert-Butoxycarbonyl-4-{2-fluoro-4-[(4-hydroxy-2-methyl-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-pentanedioic acid di-tert-butyl ester

(S)-2-((S)-4-tert-Butoxycarbonyl-4-{4-[(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-pentanedioic acid di-tert-butyl ester

Refernces

• 1、 Bader,Rosowsky. "First use of the taylor pteridine synthesis as a route to polyglutamate derivatives of antifolates". . p. 3386 - 3391. Retrieved 2007/10/02.
• 2、 Pawelczak, Krzysztof,Jones, Terence R.,Kempny, Michal,Jackman, Ann L.,Newell, David R.,et al.. "Quinazoline Antifolates Inhibiting Thymidylate Synthase: Synthesis of Four Oligo(L-γ-glutamyl) Conjugates of N10-Propargyl-5,8-dideazafolic Acid and Their Enzyme Inhibition". . p. 160 - 165. Retrieved 2007/10/02.