2',3'-Dideoxy-2',3'-didehydroinosine

Base Information

• Chemical Name: 2',3'-Dideoxy-2',3'-didehydroinosine
• CAS No.: 42867-68-5
• Molecular Formula: C10H10N4O3
• Molecular Weight: 234.214
• Hs Code.: 2934999090
• Mol file: 42867-68-5.mol

Synonyms:9-[(2R,5S)-5-(Hydroxymethyl)-2,5-dihydrofuran-2-yl]-9H-purin-6-ol;9H-purin-6-ol, 9-[(2R,5S)-2,5-dihydro-5-(hydroxymethyl)-2-furanyl]-;Inosine, 2',3'-didehydro-2',3'-dideoxy-;

Chemical Property of 2',3'-Dideoxy-2',3'-didehydroinosine

Chemical Property:

• Boiling Point: 604.8°C at 760 mmHg
• PKA: 8.92±0.70(Predicted)
• Flash Point: 319.6 °C
• PSA: 93.03000
• Density: 1.74 g/cm³
• LogP: -0.43450
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

2’,3’-Didehydrodidanosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2’,3’-Didehydrodidanosine (Didanosine EP Impurity F) is an impurity of Didanosine (D440950), which used as an antiviral agent. Classed as an anti-retroviral drug used in the treatment of HIV in ART therapy, it also may increase acetaminophen related hepatotoxicity by enhancing mitochrondrial dysfunction (2).

Technology Process of 2',3'-Dideoxy-2',3'-didehydroinosine

There total 16 articles about 2',3'-Dideoxy-2',3'-didehydroinosine 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: 99.0%

N1,5'-O-di-p-methoxybenzyl-2',3'-didehydro-2',3'-dideoxyinosine → 2',3'-didehydro-2',3'-dideoxyinosine (42867-68-5)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; at 20 ℃;

DOI:10.1080/15257770701508414

Reference yield: 92.0%

2',3'-bis-O-[(methylthio)thiocarbonyl]inosine (810694-82-7) → 2',3'-didehydro-2',3'-dideoxyinosine (42867-68-5)

Guidance literature:

With N-ethylpiperidine hypophosphite; triethyl borane; In tetrahydrofuran; 1,4-dioxane; hexane; at 20 ℃; for 1h;

Reference yield: 89.0%

2',3'-didehydro-5'-O-(2,5,5-trimethyl-1,3-dioxolan-4-on-2-yl)-2',3'-dideoxyinosine (142504-05-0) → 2',3'-didehydro-2',3'-dideoxyinosine (42867-68-5)

Guidance literature:

With ammonia; In methanol; at 20 ℃; for 12h; Saturated solution;

DOI:10.1080/15257770.2014.898070

upstream raw materials:

5'-O-(tert-butyldimethylsilyl)-2',3'-didehydro-2',3'-dideoxyinosine

1-(5-O-Acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)hypoxanthine

2-Acetoxy-2-methyl-propionic acid (2S,5R)-5-(6-oxo-1,6-dihydro-purin-9-yl)-2,5-dihydro-furan-2-ylmethyl ester

2',3'-O-(1-methoxyethylidene)inosine

Downstream raw materials:

Dideoxyinosine

Refernces

• 1、 Torii, Takayoshi,Izawa, Kunisuke,Cho, Dae Hyan,Jang, Doo Ok. "Synthesis of 2′,3′-dideoxyinosine via radical deoxygenation". . p. 985 - 988. Retrieved 2008/03/28.
• 2、 -. "INOSINE DERIVATIVE AND PROCESS FOR PRODUCING THE SAME". Page/Page column 12. . Retrieved 2010/11/08.