3'-Fluoro-3'-deoxythymidine Monophosphate

Base Information

• Chemical Name: 3'-Fluoro-3'-deoxythymidine Monophosphate
• CAS No.: 25520-83-6
• Molecular Formula: C10H14FN2O7P
• Molecular Weight: 324.203
• Mol file: 25520-83-6.mol

Synonyms:2’,3’-dideoxy-3’-fluoro-5-methyluridine 5’-(Dihydrogen Phosphate);3’-Deoxy-3’-fluorothymidine-5’-monophosphate;3’-Deoxy-3’-fluoro-5’-thymidylic Acid;3’-Deoxy-3’-fluorothymidine Monophosphate;3’-Fluoro-3’-deoxythymidine Monophosphate

Chemical Property of 3'-Fluoro-3'-deoxythymidine Monophosphate

Chemical Property:

• PSA: 140.66000
• LogP: -0.42010

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A thymidine-5?O-monophosphate analogue as inhibitors of Mycobacterium tuberculosis thymidylate kinase.

Technology Process of 3'-Fluoro-3'-deoxythymidine Monophosphate

There total 5 articles about 3'-Fluoro-3'-deoxythymidine Monophosphate 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: 81.0%

alovudine (25526-93-6) → phosphoric acid mono[3-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahyrofuran-2-ylmethyl] ester (25520-83-6)

Guidance literature:

With tris(p-nitrophenyl)phosphate; at 50 ℃; Erwina herbicola 47/3 cells;

DOI:10.1007/BF00598099

Reference yield:

1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine (42214-24-4) → phosphoric acid mono[3-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahyrofuran-2-ylmethyl] ester (25520-83-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 17 percent / NaOH

2: DAST; pyridine / CH₂Cl₂

3: aq. AcOH / 90 °C

4: POCl₃; (MeO)3PO

With pyridine; trimethyl phosphite; sodium hydroxide; acetic acid; 4,4'-diaminostilbene-2,2'-disulfonic acid; trichlorophosphate; In dichloromethane;

DOI:10.1016/S0960-894X(02)00551-6

Reference yield:

5'-O-tritylthymidine (7791-71-1) → phosphoric acid mono[3-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahyrofuran-2-ylmethyl] ester (25520-83-6)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine

2: 17 percent / NaOH

3: DAST; pyridine / CH₂Cl₂

4: aq. AcOH / 90 °C

5: POCl₃; (MeO)3PO

With pyridine; trimethyl phosphite; sodium hydroxide; acetic acid; 4,4'-diaminostilbene-2,2'-disulfonic acid; trichlorophosphate; In dichloromethane;

DOI:10.1016/S0960-894X(02)00551-6

upstream raw materials:

alovudine

3'-Fluoro-5'-O-trityl-deoxythymidine

1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine

5'-O-tritylthymidine

Refernces

• 1、 Zinchenko, A. I.,Barai, V. N.,Mikhailopulo, I. A.. "ENZYMATIC 5'-MONOPHOSPHORYLATION OF MODIFIED NUCLEOSIDES". . p. 626 - 627. Retrieved 2007/10/02.