156407-85-1

Basic information

• Product Name: [1R-(1alpha,2alpha,3beta)]-3-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)-4-cyclopentene-1,2-diol
• Synonyms: Neplanocin A; (-)-9-[trans-2,trans-3-Dihydroxy-4-(hydroxymethyl)cyclopent-4-enyl]adenine
• CAS NO: 156407-85-1
• Molecular Formula: C₁₁H₁₃N₅O₃
• Molecular Weight: 263.25796
• Mol File: 156407-85-1.mol
• Article Data: 23

Chemical Properties

• CAS DataBase Reference: [1R-(1alpha,2alpha,3beta)]-3-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)-4-cyclopentene-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: [1R-(1alpha,2alpha,3beta)]-3-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)-4-cyclopentene-1,2-diol(156407-85-1)
• EPA Substance Registry System: [1R-(1alpha,2alpha,3beta)]-3-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)-4-cyclopentene-1,2-diol(156407-85-1)

Safety Data

• Hazardous Substances Data: 156407-85-1(Hazardous Substances Data)

Upstream product

• 89291-82-7 (-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>adenine 
• 85390-40-5 methyl (1R,2S,3S,4R)-2,3-<(dimethylmethylene)dioxy>-4-<((methoxymethyl)oxy)methyl>-4-(phenylseleno)cyclopentane-1-carboxylate 
• 85390-41-6 (1R,2S,3S,4R)-2,3-<(dimethylmethylene)dioxy>-4-<((methoxymethyl)oxy)methyl>-1-<(methoxycarbonyl)amino>-4-(phenylseleno)cyclopentane 
• 85390-43-8 (1R,2S,3R)-1-(5-amino-6-chloro-4-pyridinylamino)-4-<((methoxymethyl)oxy)methyl>-2,3-<(dimethylmethylene)dioxy>-4-cyclopentene 
• 85846-80-6 5-O-benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone 
• 160343-78-2 (3aR,6aR)-6-{{[(1,1-dimethylethyl)dimethylsilyl]oxy}methyl}-3a,6a-dihydro-2,2-dimethyl-4H-cyclopenta[d]-1,3-dioxol-4-one 
• 160343-79-3 (3aS,4S,6aR)-6-{{[(1,1-dimethylethyl)dimethylsilyl]oxy}methyl}-3a,6a-dihydro-2,2-dimethyl-4H-cyclopenta[d]-1,3-dioxol-4-ol 
• 162126-83-2 (3aS,4S,6aR)-6-hydroxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol 
• 197227-13-7 9-{(3aS,4R,6aR)-6-{{[(1,1-dimethylethyl)dimethylsilyl]oxy}methyl}-3a,6a-dihydro-2,2-dimethyl-4H-cyclopenta[d]-1,3-dioxol-4-yl}-9H-purin-6-amine 
• 377748-77-1 (1'S,2'R,3'S)-9-[2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-yl]adenine 
• 104010-72-2 (3aS,6aS)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one 
• 115509-13-2 (3aR,6aR)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one 
• 377748-50-0 (1S,2R,3R)-1-(tert-butoxymethyl)-2,3-(isopropylidenedioxy)-4-cyclopenten-1-ol 
• 377748-55-5 (2S,3S)-2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-one 

Downstream Products

• 84207-68-1 N⁶,6'-dibenzoylneplanocin A 
• 78216-79-2 ara-neplanocin A 
• 138571-54-7 6'-(R)-methylneplanocin A 
• 142888-07-1 C₂₇H₂₅N₅O₅ 

Relevant articles and documents

Syntheses of cyclopentyl nucleoside (?)-neplanocin A through tetrazole-fragmentation from cyanophosphates

We recently reported a novel synthetic method for five-membered unsaturated cyclic compounds from ketones involving cyanophosphates (CPs) under neutral conditions, in which alkylidene carbenes generated through tetrazole-fragmentation undergo [1,5]-C–H in

Synthesis of (-)-Neplanocin A via C-H Insertion of Alkylidenecarbene

(-)-Neplanocin A, a naturally occurring carbocyclic nucleoside was synthesized via C-H insertion reaction of the alkylidenecarbene, which was generated by the reaction of lithiotrimethylsilyldiazomethane and the ketone derived from D-ribose.

Total synthesis of neplanocin A

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Total synthesis of carbocyclic nucleoside (+)-neplanocin A

Asymmetric total synthesis of (+)-neplanocin A was concisely achieved from readily available d-galactose via the regioselective and diastereoselective amination of carbocyclic polybenzyl ether using chlorosulfonyl isocyanate and intramolecular olefin meta