2'-Bromo-2'-deoxy-D-uridine

Base Information

• Chemical Name: 2'-Bromo-2'-deoxy-D-uridine
• CAS No.: 4753-02-0
• Molecular Formula: C9H11 Br N2 O5
• Molecular Weight: 307.1
• Mol file: 4753-02-0.mol

Synonyms:2'-Bromo-2'-deoxyuridine

Chemical Property of 2'-Bromo-2'-deoxy-D-uridine

Chemical Property:

• PSA: 104.55000
• LogP: -1.44930

Purity/Quality:

97% ^*data from raw suppliers

2''-Bromo-2''-deoxy-D-uridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2'-Bromo-2'-deoxy-D-uridine

There total 5 articles about 2'-Bromo-2'-deoxy-D-uridine 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: 71.0%

2,2'-Anhydrouridine (3736-77-4) → 2'-bromo-2'-deoxyuridine (4753-02-0)

Guidance literature:

With trifluoroacetic acid; lithium bromide; In N,N-dimethyl-formamide; at 105 ℃; for 3h;

DOI:10.1021/ja962117m

Reference yield:

1-(3,5-di-O-acetyl-2-bromo-2-deoxy-β-D-ribofuranosyl)-uracil (19325-92-9) → 2'-bromo-2'-deoxyuridine (4753-02-0)

Guidance literature:

With sodium methylate; In methanol; for 2h; Ambient temperature;

Reference yield:

uridine (58-96-8) → 2'-bromo-2'-deoxyuridine (4753-02-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / acetic acid / 1.5 h / 100 °C

2: 0.51 g / Sodium methoxide / methanol / 2 h / Ambient temperature

With sodium methylate; In methanol; acetic acid;

upstream raw materials:

1-(3,5-di-O-acetyl-2-bromo-2-deoxy-β-D-ribofuranosyl)-uracil

2,2'-Anhydrouridine

uridine

Downstream raw materials:

1-((2S,4R,5S)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

Thiocarbonic acid O-[(2R,3R,4R,5R)-4-bromo-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester O-phenyl ester

Refernces

• 1、 Robins, Morris J.,Wnuk, Stanislaw F.,Hernández-Thirring, Amelia E.,Samano, Mirna C.. "Nucleic acid related compounds. 91. Biomimetic reactions are in harmony with loss of 2'-substituents as free radicals (not anions) during mechanism-based inactivation of ribonucleotide reductases. Differential interactions of azide, halogen, and alkylthio". . p. 11341 - 11348. Retrieved 2007/10/03.
• 2、 Lee,Knaus,Wiebe. "21-[82Br]-bromo-21-deoxyuridine for tumor uptake studies". . p. 167 - 168. Retrieved 2007/10/09.