3',5'-DI-O-ACETYL-5-BROMO-2'-DEOXY-D-URIDINE

Base Information

• Chemical Name: 3',5'-DI-O-ACETYL-5-BROMO-2'-DEOXY-D-URIDINE
• CAS No.: 6161-23-5
• Molecular Formula: C13H15BrN2O7
• Molecular Weight: 391.175
• Mol file: 6161-23-5.mol

Synonyms:3',5'-DI-O-ACETYL-5-BROMO-2'-DEOXY-D-URIDINE

Chemical Property of 3',5'-DI-O-ACETYL-5-BROMO-2'-DEOXY-D-URIDINE

Chemical Property:

• Melting Point: 148-150°C
• Refractive Index: 1.586
• PKA: 7.73±0.10(Predicted)
• PSA: 116.69000
• Density: 1.667g/cm³
• LogP: 0.08140
• Storage Temp.: Refrigerator

Purity/Quality:

97% ^*data from raw suppliers

3’,5’-Di-O-acetyl-5-bromo-2’-deoxyuridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3’, 5’-Di-O-acetyl-5-bromo-2’-deoxyuridine (cas# 6161-23-5) is a compound useful in organic synthesis.

Technology Process of 3',5'-DI-O-ACETYL-5-BROMO-2'-DEOXY-D-URIDINE

There total 3 articles about 3',5'-DI-O-ACETYL-5-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: 95.0%

3',5'-di-O-acetyl-2'-deoxyuridine (13030-62-1) → 1-(3,5-di-O-acetyl-β-D-2-deoxyribofuranosyl)-5-bromouracil (6161-23-5)

Guidance literature:

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

DOI:10.1139/v94-256

Reference yield: 95.0%

acetic anhydride (108-24-7) + 5-bromo-2'-deoxyuridine (59-14-3,723-73-9) → 1-(3,5-di-O-acetyl-β-D-2-deoxyribofuranosyl)-5-bromouracil (6161-23-5)

Guidance literature:

With 1-methyl-1H-imidazole; In acetonitrile; at 60 ℃; for 1h;

DOI:10.1021/ol701826x

Reference yield:

→ 1-(3,5-di-O-acetyl-β-D-2-deoxyribofuranosyl)-5-bromouracil (6161-23-5)

Guidance literature:

2'-Deoxyuridin IIIc, N-Bromsuccinimid;

upstream raw materials:

3',5'-di-O-acetyl-2'-deoxyuridine

acetic anhydride

5-bromo-2'-deoxyuridine

Downstream raw materials:

5-bromo-4-thio-2'-deoxyuridine

3-(3',5'-di-O-tert-butyl-dimethyl-silane-d-ribofuranosyl)-9-(2-N-benzylcarbamyl-ethoxy)-1,3-diaza-7-O-pivaloyl-2-oxophenoxadine

3-(2'-deoxy-D-ribofuranosyl)-9-(2-N-benzylcarbamylethoxy)-1,3-diaza-7-O-pivaloyl-2-oxophenoxadine

N-[4-(2-N-benzylcarbamylethoxy-4,6-dihydroxyphenyl)]-2'-deoxy-5-bromouridine

Refernces

• 1、 Teppang, Kristine L.,Lee, Raymond W.,Burns, Dillon D.,Turner, M. Benjamin,Lokensgard, Melissa E.,Cooksy, Andrew L.,Purse, Byron W.. "Electronic Modifications of Fluorescent Cytidine Analogues Control Photophysics and Fluorescent Responses to Base Stacking and Pairing". . p. 1249 - 1259. Retrieved 2019/01/04.
• 2、 Zhang, Xiaohui,Wang, Jian,Xu, Yao-Zhong. "Systematic assignment of NMR spectra of 5-substituted-4-thiopyrimidine nucleosides". . p. 523 - 529. Retrieved 2013/09/02.