11-oxahomofolic acid

Base Information

• Chemical Name: 11-oxahomofolic acid
• CAS No.: 72254-43-4
• Molecular Formula: C20H20 N6 O7
• Molecular Weight: 456.4088
• Mol file: 72254-43-4.mol

Synonyms:11-Oxahomofolicacid

Chemical Property of 11-oxahomofolic acid

Chemical Property:

• PSA: 211.47000
• Density: 1.63g/cm³
• LogP: 0.69790

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 11-oxahomofolic acid

There total 21 articles about 11-oxahomofolic acid 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: 66.0%

(S)-2-{4-[2-(2-Amino-4-hydroxy-7,8-dihydro-pteridin-6-yl)-ethoxy]-benzoylamino}-pentanedioic acid diethyl ester → 11-oxahomofolic acid (72254-43-4)

Guidance literature:

With potassium permanganate; In ethanol; for 0.333333h; Ambient temperature;

DOI:10.1021/jm00141a010

Reference yield:

diethyl-L-glutamate hydrochloride (1118-89-4) → 11-oxahomofolic acid (72254-43-4)

Guidance literature:

Multi-step reaction with 7 steps

1: N-methylmorpholine, isobutyl chloroformate / 1.) DMF, 20 min, 2.) DMF, RT, 18 h

2: H₂ / 5percent Pd/C / methanol / 18 h / 1292.9 Torr

3: 2.) N-methylmorpholine / 1.) methanol, reflux, 1.5 h, 2.) methanol, reflux, 3 h

4: 1N HCl, trifluoroacetic acid / 0.33 h / 55 °C

5: sodium dithionite / dimethylformamide; H₂O / 0.5 h

6: 0.1N NaOH / 1.5 h

7: 66 percent / 5percent KMnO₄ / ethanol / 0.33 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; potassium permanganate; sodium dithionite; hydrogen; trifluoroacetic acid; isobutyl chloroformate; palladium on activated charcoal; In methanol; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00141a010

Reference yield:

1-azido-4--2-butanone (78520-73-7) → 11-oxahomofolic acid (72254-43-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 82 percent / p-toluenesulfonic acid monohydrate / benzene / 6 h / Heating

2: 93.5 percent / 0.5 N NaOH / acetonitrile / 18 h / Ambient temperature

3: N-methylmorpholine, isobutyl chloroformate / 1.) DMF, 20 min, 2.) DMF, RT, 18 h

4: H₂ / 5percent Pd/C / methanol / 18 h / 1292.9 Torr

5: 2.) N-methylmorpholine / 1.) methanol, reflux, 1.5 h, 2.) methanol, reflux, 3 h

6: 1N HCl, trifluoroacetic acid / 0.33 h / 55 °C

7: sodium dithionite / dimethylformamide; H₂O / 0.5 h

8: 0.1N NaOH / 1.5 h

9: 66 percent / 5percent KMnO₄ / ethanol / 0.33 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; potassium permanganate; sodium dithionite; hydrogen; toluene-4-sulfonic acid; trifluoroacetic acid; isobutyl chloroformate; palladium on activated charcoal; In methanol; ethanol; water; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/jm00141a010

upstream raw materials:

diethyl-L-glutamate hydrochloride

1-azido-4--2-butanone

1-azido-4-(p-carboxyphenoxy)-2-butanone ethylene ketal

1-azido-4--2-butanone ethylene ketal

Refernces

• 1、 Nair, M. G.,Saunders, Colleen,Chen, Shiang-Yuan,Kisliuk, Roy L.,Gaumont, Y.. "Folate Analogues in the C9-N10 Bridge Region. 14. 11-Oxahomofolic Acid, a Potential Antitumor Agent". . p. 59 - 65. Retrieved 2007/10/02.