156407-85-1

Upstream product

• 85390-44-9 9-<(1R,2S,3R)-4-<((methoxymethyl)oxy)methyl>-2,3-<(dimethylmethylene)dioxy>-4-cyclopenten-1-ylk>adenine 
• 128165-50-4 9-<(1'R,4'R,5'S)-3-(tert-butoxymethyl)-4,5-(cyclohexylidenedioxy)-2-cyclopenten-1-yl>adenine 
• 79386-50-8 (3'R,4'S,5'R)-3'-(6-aminopurin-9-yl)-1'-hydroxymethyl-4',5'-O-isopropylidene-cyclopent-1'-en-4',5'-diol 
• 89291-82-7 (-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>adenine 
• 142888-05-9 C₂₃H₄₀FN₅O₄Si₂ 
• 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 
• 377748-85-1 (1'R,2'S,3'R)-9-[2,3-(isopropylidenedioxy)-4-(tert-butoxymethyl)-4-cyclopenten-1-yl]adenine 
• 952418-11-0 (1R,4R,5S)-9-[3-(tert-butyldiphenylsilyloxymethyl)-4,5-isopropylidenedioxy-2-cyclopenten-1-yl]-N⁶,N⁶-bis(tert-butoxycarbonyl)adenine 
• 952418-12-1 (1R,4R,5S)-9-[3-(tert-butyldiphenylsilyloxymethyl)-4,5-isopropylidenedioxy-2-cyclopenten-1-yl]adenine 
• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 10257-32-6 D-ribose 
• 96690-02-7 5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose 
• 303963-93-1 (3aS,4S,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-ol 
• 309947-86-2 N⁶,N⁶-bis(tert-butoxycarbonyl)adenine 

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 academic research and scientific papers

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

A concise synthesis of (-)-neplanocin A

A concise stereocontrolled route to (-)-neplanocin A, a naturally occurring carbocyclic nuleoside, has been developed by employing lipase- mediated kinetic resolution.

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.

A novel route to a chiral building block for the preparation of cyclopentenyl carbocyclic nucleosides. Synthesis and anticancer activity of enantiomeric neplanocins A

The synthesis of both enantiomers of 3-[(tert-butyldimethylsilyl)oxy]methyl-4,5-O-isopropylidenecyclopent-2-en-1-ol was accomplished in six steps based on optically inactive dimethyl meso-tartrate. This key intermediate in the synthesis of cyclopentenyl carbocyclic nucleosides was subsequently applied in the preparation of enantiomeric neplanocins A. The toxic effect of these compounds was investigated for a series of suspension and adherent cancer cell lines and normal human fibroblasts. (-)-Neplanocin A ((-)-NPA) was more toxic against all tested cancer cell lines than its dextrorotary counterpart. The highest toxicity with IC50 values of 7 and 10 μM was observed for the MOLT-4 and A431 cells, respectively. Moreover, (-)-NPA also induced apoptosis in A431 cell while this effect was not observed for (+)-NPA. This journal is

Structure-Activity Relationships of Neplanocin A Analogues as S -Adenosylhomocysteine Hydrolase Inhibitors and Their Antiviral and Antitumor Activities

On the basis of the potent inhibitory activity of neplanocin A (1) against S-adenosylhomocysteine (AdoHcy) hydrolase, we analyzed the comprehensive structure-activity relationships by modifying the adenine and carbasugar moiety of 1 to find the pharmacoph

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

A convergent approach for the synthesis of ara-neplanocin a analogues under subzero microwave assisted conditions

A convergent strategy for the synthesis of ara-neplanocin A analogues has been developed. Microwave assisted Mitsunobu reaction proved to be an essential tool both for the 2' - hydroxy inversion and for the coupling reaction with the heterocyclic bases. The exploitation of the present approach allowed generating a family of ara-neplanocins which biological potential is still unexplored.

Synthesis of (-)-neplanocin A with the highest overall yield via an efficient Mitsunobu coupling

Neplanocin A was synthesized in very high isolated yield and purity, in 10 steps from d-ribose via an efficient Mitsunobu coupling using N6-bis-Boc-protected adenine. In fact, this synthesis is a short pathway to enantiopure neplanocin A giving

An improved approach to chiral cyclopentenone building blocks. Total synthesis of pentenomycin I and neplanocin A

An improved approach to enantiomerically pure hydroxylated cyclopentenones is reported here, which involves intramolecular nitrone cycloaddition of sugar-derived chiral pent-4-enals and hex-5-en-ones-2 followed by N-O bond cleavage, quaternization of the amine thus produced, and finally oxidative elimination of the amino group. Synthesis of pentenomycin I and neplanocin A is described following this methodology.

Enantiomeric synthesis of D- and L-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus

Enantiomeric synthesis of D- and L-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus are described. The key intermediate (-)- and (+)-cyclopentenyl alcohols (7 and 15) were prepared from D-γ-ribonolactone and D-ribose,