151359-36-3

Basic information

• Product Name: 9-[(2S,3R,4R)-(5,4-dihydroxy-2,3-isopropylidenedioxy)pentyl]adenine
• Synonyms: 9-[(2S,3R,4R)-(5,4-dihydroxy-2,3-isopropylidenedioxy)pentyl]adenine
• CAS NO: 151359-36-3
• Molecular Weight: 309.325
• Mol File: 151359-36-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 9-[(2S,3R,4R)-(5,4-dihydroxy-2,3-isopropylidenedioxy)pentyl]adenine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-[(2S,3R,4R)-(5,4-dihydroxy-2,3-isopropylidenedioxy)pentyl]adenine(151359-36-3)
• EPA Substance Registry System: 9-[(2S,3R,4R)-(5,4-dihydroxy-2,3-isopropylidenedioxy)pentyl]adenine(151359-36-3)

Safety Data

• Hazardous Substances Data: 151359-36-3(Hazardous Substances Data)

Upstream product

• 5167-12-4 2',3'-isopropylideneadenosine-1-oxide 
• 958-09-8 2'-deoxy-D-adenosine 
• 58-61-7 adenosine 
• 10526-27-9 2',3'-O-(isopropylidene)-5'-O-(triphenylmethyl)uridine 

Downstream Products

• 197227-08-0 N-{9-[(4S,5R)-5-((R)-1,2-Dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl]-9H-purin-6-yl}-benzamide 
• 156407-85-1 (+)-neplanocin A 
• 197227-10-4 N-(9-{(4S,5R)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl}-9H-purin-6-yl)-benzamide 
• 38946-73-5 4-(6-amino-purin-9-yl)-2,3-dihydroxy-butyric acid 
• 81739-10-8 9-(2S,3R)-erythro-(4-O-p-toluenesulfonyl-2,3-O-isopropylidene-2,3,4-trihydroxybutyl)adenine 

Relevant articles and documents

Ribofuranose-ring cleavage of purine nucleosides with diisobutylaluminum hydride: Convenient method for the preparation of purine acyclonucleosides

The reaction of 2',3'-O-isopropylidene protected purine nucleosides with diisobutylaluminum hydride (DIBAL-H) caused the reductive cleavage of the C- l'-O-4' bond to give the corresponding 9-D-ribitylpurines. The ring cleavage of inosine 1a, thioinosine 1f, and their derivatives having an alkyl group at the O6 or S6-position 1c, e, and g proceeded smoothly to afford the corresponding ribityl derivatives 2a,f,c,e, and g, whereas N-methylated adenosine derivatives 1k and l remarkably resisted the DIBAL-H reduction. 5'- Deoxy and 5'-chloro-5'-deoxy derivatives 1b, d,i, and j also underwent reductive cleavage at the sugar moiety under similar conditions. An acyclic analog of guanosine 6, which is of biological interest, was prepared from a guanosine derivative 5 in a similar way. The present methodology for the synthesis of purine acyclonucleosides was also applied to the preparation of an acyclic analog 17 of neplanocin A.