2'-DEOXY-3',5'-DI-O-ACETYLGUANOSINE

Base Information

• Chemical Name: 2'-DEOXY-3',5'-DI-O-ACETYLGUANOSINE
• CAS No.: 69992-10-5
• Molecular Formula: C14H17 N5 O6
• Molecular Weight: 351.319
• Mol file: 69992-10-5.mol

Synonyms:2'-Deoxy-3',5'-di-O-acetylguanosine;2'-Deoxyguanosine 3',5'-diacetate; 3',5'-Di-O-acetyldeoxyguanosine;3',5'-O-Diacetyl-2'-deoxyguanosine; NSC 76761

Chemical Property of 2'-DEOXY-3',5'-DI-O-ACETYLGUANOSINE

Chemical Property:

• Vapor Pressure: 1.46E-15mmHg at 25°C
• Melting Point: >300°C
• Boiling Point: 625.5°C at 760 mmHg
• Flash Point: 332.1°C
• PSA: 151.42000
• Density: 1.72g/cm³
• LogP: 0.06530
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

2’-Deoxy-3’,5’-di-O-acetylguanosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2’-Deoxy-3’,5’-di-O-acetylguanosine reacts with hypobromous acid (HOBr) to form a major product, spiroiminodihydantoin.

Technology Process of 2'-DEOXY-3',5'-DI-O-ACETYLGUANOSINE

There total 8 articles about 2'-DEOXY-3',5'-DI-O-ACETYLGUANOSINE 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%

acetic anhydride (108-24-7) + 2'-Deoxyguanosine (961-07-9) → 3',5'-di-O-acetyl-2'-deoxyguanosine (69992-10-5)

Guidance literature:

With dmap; triethylamine; In acetonitrile; at 20 ℃; for 0.0833333h;

DOI:10.1016/j.bmcl.2011.09.104

Reference yield: 95.2%

acetic anhydride (108-24-7) + 2'-deoxyguanosine (961-07-9) → 3’,5’-O-diacetyl-2’-deoxyguanosine (69992-10-5)

Guidance literature:

With dmap; triethylamine; In acetonitrile; at 20 ℃; for 2h;

DOI:10.1039/c3md00159h

Reference yield: 90.0%

acetic anhydride (108-24-7) + 2'-deoxyguanosine monohydrate → 3',5'-di-O-acetyl-2'-deoxyguanosine (69992-10-5)

Guidance literature:

With pyridine; at 20 ℃; for 0.75h;

DOI:10.1016/j.bmc.2010.04.064

upstream raw materials:

acetic anhydride

6-O-(3,5-dichlorophenyl)-2-N-phenylacetyl-2'-deoxyguanosine

2'-Deoxyguanosine

2'-deoxyguanosine

Downstream raw materials:

2'-deoxy-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-O⁶-[2-(4-nitrophenyl)ethyl]guanosine

2'-deoxy-5'-O-(monomethoxytrityl)-N²-<2-(4-nitrophenyl)ethoxycarbonyl>-O⁶-<2-(4-nitrophenyl)ethyl>guanosine

2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N²-[2-(4-nitrophenyl)ethoxycarbonyl]-O⁶-[2-(4-nitrophenyl)ethyl]guanosine

2'-deoxy-O⁶-methyl-N²-[2-(4-nitrophenyl)ethoxycarbonyl]guanosine

Refernces

• 1、 Koole,Buck,Kanters,Schouten. "Molecular conformation of 2'-deoxy-3',5'-di-O-acetyl guanosine. Crystal structure and high resolution proton nuclear magnetic resonance investigations". . p. 2634 - 2639. Retrieved 1988.
• 2、 -. "NUCLEOTIDE PRODRUGS". Paragraph 0149; 0151; 0152. . Retrieved 2019/07/20.
• 3、 Von Watzdorf, Janina,Leitner, Kim,Marx, Andreas. "Modified Nucleotides for Discrimination between Cytosine and the Epigenetic Marker 5-Methylcytosine". supporting information. p. 3229 - 3232. Retrieved 2016/03/12.