84408-37-7

Basic information

• Product Name: Desciclovir
• Synonyms: Desciclovir;2-[(2-Amino-9H-purin-9-yl)methoxy]ethanol;6-Deoxyacyclovir;A-515U;Deoxyaciclovir
• CAS NO: 84408-37-7
• Molecular Formula: C8H11 N5 O2
• Molecular Weight: 209.21
• Mol File: 84408-37-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 529.8°C at 760 mmHg
• Flash Point: 274.2°C
• Appearance: /
• Density: 1.61g/cm³
• Vapor Pressure: 4.72E-12mmHg at 25°C
• Refractive Index: 1.725
• CAS DataBase Reference: Desciclovir(CAS DataBase Reference)
• NIST Chemistry Reference: Desciclovir(84408-37-7)
• EPA Substance Registry System: Desciclovir(84408-37-7)

Safety Data

• Hazardous Substances Data: 84408-37-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H11N5O2/c9-8-10-3-6-7(12-8)13(4-11-6)5-15-2-1-14/h3-4,14H,1-2,5H2,(H2,9,10,12)

Upstream product

• 92924-35-1 9-<(2-acetoxyethoxy)methyl>-2-amino-9H-purine 
• 74-89-5 methylamine 
• 120356-09-4 9-<(2-acetoxyethoxy)methyl>-2-acetylamino-9H-purine 
• 59277-92-8 1-(2-amino-6-chloro-purin-9-ylmethoxy)-2-benzoyloxy-ethane 
• 75128-73-3 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one 
• 102728-64-3 9-[(acetoxyethoxy)methyl]guanine 
• 81777-48-2 9-<(2-acetoxyethoxy)methyl>-2-amino-6-chloro-9H-purine 
• 10310-21-1 2-Amino-6-chloropurin 
• 452-06-2 9H-purin-2-amine 
• 158665-14-6 2-amino-6-(4-chlorophenylsulfanyl)-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine 
• 158665-16-8 9-<(2-acetoxyethoxy)methyl>-2-amino-6-(4-chlorophenylthio)-9H-purine 
• 158665-15-7 2-amino-6-<(4-chlorophenyl)sulfanyl>purine 
• 6979-94-8 2',3',5'-tri-O-acetyl-guanosine 
• 16321-99-6 2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine 

Relevant articles and documents

Conversion of guanosine into acyclovir and its 6-deoxy derivative

2-amino-6-(4-chlorophenylthio)-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl) purine 11, which is readily prepared by allowing the corresponding 6-chloro-compound 10 to react with 4-chloro(thiophenol) and triethylamine in methanol solution at room temperature, reacts with boron trifluoride diethyl etherate in boiling dichloromethane solution to give 2-amino-6-(4-chlorophenylthio)-9H-purine 12 in high isolated yield. 9-[(2-acetoxyethoxy)methyl]-2-amino-6-(4-chlorophenylthio)-9H-purine 13, prepared from the latter aglycone 12 in good yield, is converted by a four-step process into acyclovir 1 and by a two-step process into 6-deoxyacyclovir 2.

Process for preparing purine derivates

There is disclosed a process for preparing purine derivatives of the formula I wherein, R1 represents hydrogen, CH3CO or a higher acyl,R3 represents hydrogen, CH3CO or a higher acyl, CF3CO, CCl3CO, PhCO or CH2 AR, such as benzyl or substituted benzyl, and benzoisothiazolyl-S,S-dioxide, and, Z represents OH, hydrogen or halo. Said compounds are either drugs or prodrugs for the treatment of herpes infections. There are also disclosed some novel compounds of formula I useful as prodrugs.

Method of producing acyclovir

The novel compound 6-deoxyacyclovir is enzymatically converted to acyclovir by xanthine oxidase/dehydrogenase or aldehyde oxidase in vivo, i.e. within the body of the animal being treated. The enzymatic conversion may also be effected ex vivo (i.e. in vitro) as a method of synthesizing acyclovir.