5,10-Dideazatetrahydrofolic

Base Information

• Chemical Name: 5,10-Dideazatetrahydrofolic
• CAS No.: 95693-76-8
• Molecular Formula: C21H25N5O6
• Molecular Weight: 443.459
• Mol file: 95693-76-8.mol

Synonyms:L-Glutamicacid, N-[4-[2-(2-amino-1,4,5,6,7,8-hexahydro-4-oxopyrido[2,3-d]pyrimidin-6-yl)ethyl]benzoyl]-(9CI);5,10-Dideaza-5,6,7,8-tetrahydrofolic acid;

Chemical Property of 5,10-Dideazatetrahydrofolic

Chemical Property:

• Refractive Index: 1.709
• PSA: 187.50000
• Density: 1.56 g/cm³
• LogP: 1.72700

Purity/Quality:

99% ^*data from raw suppliers

5,10-DIDEAZATETRAHYDROFOLIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 5,10-Dideazatetrahydrofolic acid (DDATHF) is a potent and selective antitumor agent that has shown promise in preclinical trials. It is structurally related to folic acid but lacks nitrogen atoms at positions 5 and 10, contributing to its unique biological activity. The development of a more efficient and convergent synthetic route using palladium-catalyzed coupling reactions has facilitated its production and the potential creation of analogs for improved antitumor applications. This advancement underscores its significance as a candidate for further anticancer drug development.

Technology Process of 5,10-Dideazatetrahydrofolic

There total 74 articles about 5,10-Dideazatetrahydrofolic 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: 87.0%

diethyl 2-acetyl-5,10-dideaza-5,6,7,8-tetrahydrofolate (95674-76-3) → N-(4-[2-(2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]-pyrimidin-6-yl)ethyl]benzoyl)-L-glutamic acid (95693-76-8)

Guidance literature:

With sodium hydroxide; In methanol; for 72h; Ambient temperature;

DOI:10.1021/jm00145a012

Reference yield: 69.0%

2-{4-[2-(2-Amino-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-6-yl)-ethyl]-benzoylamino}-pentanedioic acid diethyl ester → lometrexol (95693-76-8,106400-18-4,106400-81-1,135503-66-1)

Guidance literature:

With sodium hydroxide; In methanol; at 23 - 25 ℃; for 48h;

DOI:10.1021/jm00119a018

Reference yield:

diethyl N-(4-[2-(2-acetamido-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]benzoyl)-L-glutamate d(+)-10-camphorsulfonate → N-(4-[2-(2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]-pyrimidin-6-yl)ethyl]benzoyl)-L-glutamic acid (95693-76-8)

Guidance literature:

With sodium hydroxide; acetic acid; In methanol;

upstream raw materials:

diethyl N-<4-<<2-(pivaloylamino)-4-hydroxy-5,6,7,8-tetrahydropyrido<2,3-d>pyrimidin-6-yl>ethyl>benzoyl>-L-glutamate

L-glutamic acid

(6RS)-methyl 4-[2-(2-pivaloylamino-4(3H)-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]benzoate

4-ethenylbenzoic acid

Refernces

Convergent and efficient palladium-effected synthesis of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF)

10.1021/jo00276a023

The research details a nine-step synthesis of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF), a highly active and selective antitumor agent currently in preclinical trials. The purpose of this new synthesis method was to improve upon the original lengthy and non-convergent synthesis process, aiming to create a more efficient and convergent pathway that would allow for the preparation of congeners and analogues. The synthesis is highlighted by the use of two successive palladium-catalyzed carbon-carbon coupling reactions to form the C5-C7 and C10-aryl bonds. The conclusions of the research indicate that the new synthetic route to DDATHF is more efficient than the original method, and it provides a foundation for the synthesis of related compounds, which could potentially lead to the development of new antitumor drugs with improved clinical effectiveness.