149355-97-5

Basic information

• Product Name: 9-(5'-O-benzyl-2',3'-O-isopropylidene-β-D-ribofuranosyl)-8-azahypoxanthine
• CAS NO: 149355-97-5
• Molecular Weight: 399.406
• Mol File: 149355-97-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 9-(5'-O-benzyl-2',3'-O-isopropylidene-β-D-ribofuranosyl)-8-azahypoxanthine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-(5'-O-benzyl-2',3'-O-isopropylidene-β-D-ribofuranosyl)-8-azahypoxanthine(149355-97-5)
• EPA Substance Registry System: 9-(5'-O-benzyl-2',3'-O-isopropylidene-β-D-ribofuranosyl)-8-azahypoxanthine(149355-97-5)

Safety Data

• Hazardous Substances Data: 149355-97-5(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 149355-96-4 5-O-benzyl-2,3-O-isopropylidene-1-azido-β-D-ribofuranose 
• 107-91-5 cyanoacetic acid amide 
• 109-94-4 formic acid ethyl ester 
• 5975-09-7 2,3-O-isopropylidene-β-D-ribofuranosyl-1-azide 

Downstream Products

• 149355-98-6 5'-O-benzyl-2',3'-O-isopropylidene-8-azaadenosine 
• 10299-44-2 8-azaadenosine 
• 53458-40-5 8-Aza-2',3'-O-isopropylidene-adenosine 

Relevant articles and documents

Evaluation of the quantitative contribution of an aryl group on C(2) of 8-azaadenines to binding with adenosine deaminase: A new synthesis of 8-azaadenosine. XI

The introduction of a phenyl group on C(2) of 8-azaadenosine increases binding to the adenosine deaminase enzyme (ADA). This stability increment has been quantitatively evaluated in both 8-azaadenosines and 9-(2',3'-dihydroxypropyl)-8-azaadenines; it resulted nearly equivalent in the two series. 8-Azaadenosine has been synthesized through a new route employing fully protected β-D-ribofuranosyl-1-azide. Instead, the stability difference in 9-(n-alkyl)-8-azaadenines, owing to the inactivity of the C(2) unsubstituted compounds, could not be evaluated. Consideration of the enantioselectivity of the ADA enzyme toward chiral 9-(2',3'-dihydroxypropyl)-8-azaadenines and 9-(2',3'-dihydroxypropyl)-8-azahypoxanthines allowed the exclusion of an appreciable structural modification in the enzyme-inhibitor complex when hydrogen on C(2) is substituted by an aryl group.