11-oxahomoaminopterin

Base Information

• Chemical Name: 11-oxahomoaminopterin
• CAS No.: 78520-72-6
• Molecular Formula: C20H21 N7 O6
• Molecular Weight: 455.42404
• Hs Code.: 2933990090
• Mol file: 78520-72-6.mol

Synonyms:NSC 325304

Chemical Property of 11-oxahomoaminopterin

Chemical Property:

• PSA: 216.53000
• Density: 1.527g/cm³
• LogP: 1.80680

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 11-oxahomoaminopterin

There total 12 articles about 11-oxahomoaminopterin 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:

diethyl-L-glutamate hydrochloride (1118-89-4) → 4-amino-4-deoxy-11-oxahomoaminopterin (78520-72-6)

Guidance literature:

Multi-step reaction with 8 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 h, 2.) methanol, 2 h

4: 94.8 percent / 1N HCl, trifluoroacetic acid / 55 °C

5: sodium dithionite / dimethylformamide; H₂O / 0.5 h

6: 0.1N NaOH / 1.5 h

7: Me₂SO / dimethylformamide / 47 h

8: 0.1N NaOH / acetonitrile

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

DOI:10.1021/jm00141a010

Reference yield:

1-azido-4--2-butanone (78520-73-7) → 4-amino-4-deoxy-11-oxahomoaminopterin (78520-72-6)

Guidance literature:

Multi-step reaction with 10 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 h, 2.) methanol, 2 h

6: 94.8 percent / 1N HCl, trifluoroacetic acid / 55 °C

7: sodium dithionite / dimethylformamide; H₂O / 0.5 h

8: 0.1N NaOH / 1.5 h

9: Me₂SO / dimethylformamide / 47 h

10: 0.1N NaOH / acetonitrile

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

DOI:10.1021/jm00141a010

Reference yield:

1-azido-4-(p-carboxyphenoxy)-2-butanone ethylene ketal (78520-75-9) → 4-amino-4-deoxy-11-oxahomoaminopterin (78520-72-6)

Guidance literature:

Multi-step reaction with 8 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 h, 2.) methanol, 2 h

4: 94.8 percent / 1N HCl, trifluoroacetic acid / 55 °C

5: sodium dithionite / dimethylformamide; H₂O / 0.5 h

6: 0.1N NaOH / 1.5 h

7: Me₂SO / dimethylformamide / 47 h

8: 0.1N NaOH / acetonitrile

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

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