1-(2-O,3-O,5-O-Triacetyl-β-D-arabinofuranosyl)-2,4(1H,3H)-pyrimidinedione

Base Information

• Chemical Name: 1-(2-O,3-O,5-O-Triacetyl-β-D-arabinofuranosyl)-2,4(1H,3H)-pyrimidinedione
• CAS No.: 14057-18-2
• Molecular Formula: C15H18 N2 O9
• Molecular Weight: 370.316
• Mol file: 14057-18-2.mol

Synonyms:Uracil,1-b-D-arabinofuranosyl-,2',3',5'-triacetate (6CI,8CI); 1-(2',3',5'-Tri-O-acetyl-b-D-arabinofuranosyl)uracil;2',3',5'-Tri-O-acetylspongouridine; NSC 79269; Spongouridine,2',3',5'-triacetate

Chemical Property of 1-(2-O,3-O,5-O-Triacetyl-β-D-arabinofuranosyl)-2,4(1H,3H)-pyrimidinedione

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 142.99000
• Density: 1.43g/cm³
• LogP: -1.13950

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-(2-O,3-O,5-O-Triacetyl-β-D-arabinofuranosyl)-2,4(1H,3H)-pyrimidinedione

There total 12 articles about 1-(2-O,3-O,5-O-Triacetyl-β-D-arabinofuranosyl)-2,4(1H,3H)-pyrimidinedione 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: 100.0%

araU (3083-77-0) + acetic anhydride (108-24-7) → 1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)uracil (14057-18-2)

Guidance literature:

With dmap;

DOI:10.1021/jo9822939

Reference yield: 78.0%

N-Acetylimidazole (2466-76-4) + araU (3083-77-0) → 1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)uracil (14057-18-2)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃; for 4h; pH=8;

DOI:10.1055/s-0036-1588626

Reference yield:

O2,2'-anhydro-1-(β-D-arabinofuranosyl)uracil (292037-79-7) → 1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)uracil (14057-18-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.1 M NaOH / H₂O / Ambient temperature

2: 4-(dimethylamino)pyridine (DMAP) / 5 h / Ambient temperature

With dmap; sodium hydroxide; In water;

DOI:10.1021/jm00111a050

upstream raw materials:

araU

acetic anhydride

C₄₅H₄₆N₅O₁₆P

2,2'-Anhydrouridine

Refernces

• 1、 Lin, Kun-I.,Chiang, Li-Wu,Wu, Chien-Hung,Chen, Shao-Wei,Yu, Chung-Shan. "Synthesis of 5-radioiodoarabinosyl uridine analog for probing the HSV-1 thymidine kinase gene". . p. 563 - 568. Retrieved 2007.
• 2、 Mieczkowski, Adam,Makowska, Malgorzata,Sekula, Justyna,Tomczyk, Ewelina,Zalewska, Ewa,Nasulewicz-Goldeman, Anna,Wietrzyk, Joanna. "Bicyclic cytarabine analogues: Synthesis and investigation of antitumor properties of novel, 6-aryl- and 6-alkyl-3H-pyrrolo[2,3-d]pyrimidin-2(7H)-one arabinosides". . p. 8454 - 8461. Retrieved 2015.
• 3、 -. "PROBE OF IODINE-123 MARKER THYMIDINE (FLT)ANALOGUE [123I]-IARAU". Paragraph 0020-0021. . Retrieved 2014/03/25.