6-METHYL-3-(BETA-D-2-DEOXY-RIBOFURANOSYL)FURANO[2,3-D]PYRIMIDIN-2-ONE

Base Information

• Chemical Name: 6-METHYL-3-(BETA-D-2-DEOXY-RIBOFURANOSYL)FURANO[2,3-D]PYRIMIDIN-2-ONE
• CAS No.: 383897-60-7
• Molecular Formula: C12H14 N2 O5
• Molecular Weight: 266.25
• Mol file: 383897-60-7.mol

Synonyms:6-METHYL-3-(BETA-D-2-DEOXY-RIBOFURANOSYL)FURANO[2,3-D]PYRIMIDIN-2-ONE

Chemical Property of 6-METHYL-3-(BETA-D-2-DEOXY-RIBOFURANOSYL)FURANO[2,3-D]PYRIMIDIN-2-ONE

Chemical Property:

• PSA: 97.72000
• LogP: -0.06140

Purity/Quality:

97% ^*data from raw suppliers

6-METHYL-3-(BETA-D-2-DEOXY-RIBOFURANOSYL)FURANO[2,3-D]PYRIMIDIN-2-ONE 98.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6-METHYL-3-(BETA-D-2-DEOXY-RIBOFURANOSYL)FURANO[2,3-D]PYRIMIDIN-2-ONE

There total 3 articles about 6-METHYL-3-(BETA-D-2-DEOXY-RIBOFURANOSYL)FURANO[2,3-D]PYRIMIDIN-2-ONE 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: 95.0%

5-(1-propynyl)-2'-deoxyuridine (84558-94-1) → 3-(β-D-2-deoxyribofuranosyl)-6-methylfuro[2,3-d]pyrimidin-2-one (383897-60-7)

Guidance literature:

With copper(l) iodide; triethylamine; In methanol; for 4h; Heating;

DOI:10.1016/j.tetlet.2004.01.108

Reference yield: 50.0%

5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) + prop-1-yne (74-99-7) → 5-(1-propynyl)-2'-deoxyuridine (84558-94-1) + 3-(β-D-2-deoxyribofuranosyl)-6-methylfuro[2,3-d]pyrimidin-2-one (383897-60-7)

Guidance literature:

With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 55 - 60 ℃; for 18h;

DOI:10.1002/hlca.200390103

Reference yield:

5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) → 3-(β-D-2-deoxyribofuranosyl)-6-methylfuro[2,3-d]pyrimidin-2-one (383897-60-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / NEt₃; CuI / Pd(PPh₃)4 / dimethylformamide

2: 95 percent / NEt₃; CuI / methanol / 4 h / Heating

With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In methanol; N,N-dimethyl-formamide; 1: Sonogashira coupling / 2: Robins and Barr method;

DOI:10.1016/j.tetlet.2004.01.108

upstream raw materials:

5-Iodo-2'-deoxyuridine

prop-1-yne

5-(1-propynyl)-2'-deoxyuridine

Downstream raw materials:

Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-methyl-2-oxo-2,7-dihydro-pyrrolo[2,3-d]pyrimidin-3-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

3-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-methyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-2-one

3-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-methyl-3H-furo[2,3-d]pyrimidin-2-one

3-(β-D-2-deoxyribofuranosyl)-3,7-dihydro-6-methyl-2H-pyrrolo[2,3-d]pyrimidin-2-one

Refernces

• 1、 Berry, David A.,Jung, Kee-Yong,Wise, Dean S.,Sercel, Anthony D.,Pearson, William H.,Mackie, Hugh,Randolph, John B.,Somers, Robert L.. "Pyrrolo-dC and pyrrolo-C: Fluorescent analogs of cytidine and 2′-deoxycytidine for the study of oligonucleotides". . p. 2457 - 2461. Retrieved 2007/10/03.