2,4(1H,3H)-Pyrimidinedione, 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methyl-

Base Information

• Chemical Name: 2,4(1H,3H)-Pyrimidinedione, 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methyl-
• CAS No.: 97614-47-6
• Molecular Formula: C24H21 F N2 O7
• Molecular Weight: 468.4311432
• Mol file: 97614-47-6.mol

Synonyms:2,4(1H,3H)-Pyrimidinedione, 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-尾-D-arabinofuranosyl)-5-methyl-

Chemical Property of 2,4(1H,3H)-Pyrimidinedione, 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methyl-

Chemical Property:

• PSA: 116.69000
• LogP: 2.16310

Purity/Quality:

97% ^*data from raw suppliers

((2R,3R,4S,5R)-3-(Benzoyloxy)-4-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methylbenzoate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,4(1H,3H)-Pyrimidinedione, 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methyl-

There total 6 articles about 2,4(1H,3H)-Pyrimidinedione, 1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-methyl- 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:

2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide (97614-44-3) + 2,4-bis(trimethylsiloxy)-5-methylpyrimidine (7288-28-0) → 1-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)thymine (97614-47-6)

Guidance literature:

In tetrachloromethane; for 60h; Heating;

DOI:10.1021/jo00236a017

Reference yield:

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (97614-43-2) → 1-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)thymine (97614-47-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / hydrogen bromide; acetic acid / 1,2-dichloro-ethane / 0.5 h / 80 °C

2: acetonitrile / 0.83 h / 80 - 81 °C

With hydrogen bromide; acetic acid; In 1,2-dichloro-ethane; acetonitrile;

DOI:10.1081/SCC-120004272

Reference yield:

thymin (65-71-4,28806-14-6,691841-57-3) → 1-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)thymine (97614-47-6)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonium sulfate / acetonitrile / 20 h / Heating

2: acetonitrile / 1.5 h / Heating

With ammonium sulfate; In acetonitrile;

DOI:10.1021/jo00219a048

upstream raw materials:

2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D-arabinofuranosyl bromide

2,4-bis(trimethylsiloxy)-5-methylpyrimidine

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

2-O-(imidazolylsulfonyl)-1,3,5-tri-O-benzoyl-α-D-ribofuranose

Downstream raw materials:

(5S,6R)-1-[(2R,3S,4R,5R)]-3',5'-di-O-trityl-5,6-dihydroxy-2'-arabinofluorothymidine

(5R,6S)-1-[(2R,3S,4R,5R)]-3',5'-di-O-trityl-5,6-dihydroxy-2'-arabinofluorothymidine

1-(2-deoxy-2-fluoro-α-D-arabinofuranosyl)thymine

1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)thymine

Refernces

• 1、 Abou Assi, Hala,Lin, Yu Chen,Serrano, Israel,González, Carlos,Damha, Masad J.. "Probing Synergistic Effects of DNA Methylation and 2′-β-Fluorination on i-Motif Stability". . p. 471 - 477. Retrieved 2017/12/15.
• 2、 Alauddin, Mian M.,Conti, Peter S.,Fissekis, John D.,Watanabe, Kyoihci A.. "Synthesis of 2′-deoxy-2′-fluoro-1-β-D-arabinofuranosyl uracil derivatives: A method suitable for preparation of [18F]-labeled nucleosides". . p. 1757 - 1764. Retrieved 2007/10/03.