3',5'-DI-O-ACETYL-2'-DEOXYADENOSINE

Base Information

• Chemical Name: 3',5'-DI-O-ACETYL-2'-DEOXYADENOSINE
• CAS No.: 17318-24-0
• Molecular Formula: C14H17 N5 O5
• Molecular Weight: 335.319
• Mol file: 17318-24-0.mol

Synonyms:2'-Deoxyadenosine3',5'-diacetate; 3',5'-Di-O-acetyl-2'-deoxyadenosine; NSC 76760

Chemical Property of 3',5'-DI-O-ACETYL-2'-DEOXYADENOSINE

Chemical Property:

• Boiling Point: 557.1°Cat760mmHg
• Flash Point: 290.7°C
• PSA: 131.45000
• Density: 1.62g/cm³
• LogP: 0.77200
• Solubility.: Ethyl Acetate, Methanol

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3'',5''-Di-O-acetyl-2''-deoxyadenosine is an intermediate used in the synthesis of anti-hepatitis C virus agents.

Technology Process of 3',5'-DI-O-ACETYL-2'-DEOXYADENOSINE

There total 10 articles about 3',5'-DI-O-ACETYL-2'-DEOXYADENOSINE 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'-deoxy-D-adenosine (958-09-8,7005-15-4) → 3',5'-di-O-acetyl-2'-deoxyadenosine (17318-24-0)

Guidance literature:

With pyridine; dmap; for 4h; Ambient temperature;

DOI:10.1021/jm00020a014

Reference yield: 86.0%

N6,O3',O5'-triacetyl-2'-deoxyadenosine (4958-66-1) → 3',5'-di-O-acetyl-2'-deoxyadenosine (17318-24-0)

Guidance literature:

In methanol; at 105 ℃; for 1.5h;

DOI:10.1021/jo051256w

Reference yield: 81.0%

3',5'-di-O-acetyl N6-p-nitrophenylethoxycarbonyl-2'-deoxyadenosine (88091-71-8) → 3',5'-di-O-acetyl-2'-deoxyadenosine (17318-24-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 18h; Ambient temperature;

DOI:10.1016/0040-4020(84)85103-0

upstream raw materials:

N⁶,O^3',O^5'-triacetyl-2'-deoxyadenosine

3',5'-di-O-acetyl N⁶-p-nitrophenylethoxycarbonyl-2'-deoxyadenosine

acetic anhydride

2'-deoxy-D-adenosine

Downstream raw materials:

N⁶,N⁶-dimethyl-2'-deoxyadenosine

methyl 3-<5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-β-D-ribofuranosyl>-3,7-dihydro-7-oxo-<2,1-i>pyrimidopurine-9-carboxylate

Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[4-(5-pentyl-[1,2,4]oxadiazol-3-yl)-5-phenylsulfanylmethyleneamino-imidazol-1-yl]-tetrahydro-furan-3-yl ester

Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-5-phenylsulfanylmethyleneamino-imidazol-1-yl]-tetrahydro-furan-3-yl ester

Refernces

• 1、 Kierzek, R.,Ito, H.,Bhatt, R.,Itakura, K.. "SELECTIVE N-DEACYLATION OF N,O-PROTECTED NUCLEOSIDES BY ZINC BROMIDE". . p. 3761 - 3764. Retrieved 1981.
• 2、 De Boer,Petra,Wanner,Boesaart,Koomen. "Synthesis of fluorescent adenosine analogues". . p. 349 - 352. Retrieved 1995.
• 3、 Borowska, Justyna,Sierant, Malgorzata,Sochacka, Elzbieta,Sanna, Daniele,Lodyga-Chruscinska, Elzbieta. "DNA binding and cleavage studies of copper(II) complexes with 2′-deoxyadenosine modified histidine moiety". . p. 989 - 1004. Retrieved 2015/09/01.
• 4、 Musumeci, Domenica,Irace, Carlo,Santamaria, Rita,Montesarchio, Daniela. "Trifluoromethyl derivatives of canonical nucleosides: Synthesis and bioactivity studies". supporting information. p. 1405 - 1410. Retrieved 2013/10/08.