5-Bromouracil ribonucleoside

Base Information

• Chemical Name: 5-Bromouracil ribonucleoside
• CAS No.: 3370-69-2
• Molecular Formula: C₉H₁₁BrN₂O₆
• Molecular Weight: 323.1
• NSC Number: 82222,38296
• DSSTox Substance ID: DTXSID10870817
• Mol file: 3370-69-2.mol

Synonyms:5-Bromouracil ribonucleoside;3370-69-2;5-bromo-1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione;5-bromo-1-pentofuranosylpyrimidine-2,4(1H,3H)-dione;2,4 (1H, 3H)-Pyrimidinedione, 1-.beta.-D-arabinofuranosyl-5-bromo-;5-Bromo-1-(3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione;82950-04-7;NSC-38296;5-bro-mouridine;(-)-(5)-Bromouridine;Uracil, 1-.beta.-D-arabinofuranosyl-5-bromo-;NCIOpen2_009259;KBioGR_002441;KBioSS_002447;MLS001166624;SCHEMBL654693;KBio2_002441;KBio2_005009;KBio2_007577;KBio3_002919;DTXSID10870817;AGFIRQJZCNVMCW-UHFFFAOYSA-N;cMAP_000053;HMS1753D03;HMS2895E08;NSC38296;NSC82222;NSC-82222;STK366961;AKOS001010424;AKOS016876670;1-.beta.-Ribofuranosyl-5-bromo-uracil;PD131204;SMR000595447;SY057067;FT-0620180;A900446;Z56786795;2,3H)-Pyrimidinedione, 1-.beta.-D-arabinofuranosyl-5-bromo-

Chemical Property of 5-Bromouracil ribonucleoside

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 124.78000
• Density: 2.043g/cm³
• LogP: -2.08940
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 321.98005
• Heavy Atom Count: 18
• Complexity: 414

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=O)NC(=O)N1C2C(C(C(O2)CO)O)O)Br

Technology Process of 5-Bromouracil ribonucleoside

There total 4 articles about 5-Bromouracil ribonucleoside 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%

araU (3083-77-0) → aBrUra (957-75-5,3266-88-4,3370-69-2,38953-77-4,82950-04-7)

Guidance literature:

With N-Bromosuccinimide; sodium azide; In 1,2-dimethoxyethane; water; at 25 ℃; for 24h;

DOI:10.1139/v94-256

Reference yield:

2',3'-anhydro-1-β-D-arabinofuranosyl-5-bromo-uracil (35837-20-8) → aBrUra (957-75-5,3266-88-4,3370-69-2,38953-77-4,82950-04-7)

Guidance literature:

With triethylamine; at 70 ℃; for 5h;

DOI:10.1080/07328319908044622

Reference yield:

5-bromouridine (957-75-5) → aBrUra (957-75-5,3266-88-4,3370-69-2,38953-77-4,82950-04-7)

Guidance literature:

Multi-step reaction with 2 steps

1: diphenyl carbonate; NaHCO₃ / hexamethylphosphoric acid triamide / 0.5 h / Heating

2: Et₃N / 5 h / 70 °C

With bis(phenyl) carbonate; sodium hydrogencarbonate; triethylamine; In N,N,N,N,N,N-hexamethylphosphoric triamide; 1: Cyclization / 2: Hydrolysis;

DOI:10.1080/07328319908044622

upstream raw materials:

araU

2',3'-anhydro-1-β-D-arabinofuranosyl-5-bromo-uracil

5-bromouridine

Downstream raw materials:

(3aS)-3c-hydroxy-2t-hydroxymethyl-(3ar,9ac)-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-c]pyrimidine-6,8-dione

Refernces

• 1、 -. "Anti-HCV nucleoside derivatives". . . Retrieved 2008/06/13.
• 2、 Kumar,Wiebe,Knaus. "A mild and efficient methodology for the synthesis of 5-halogeno uracil nucleosides that occurs via a 5-halogeno-6-azido-5,6-dihydro intermediate". . p. 2005 - 2010. Retrieved 2007/10/02.