72877-50-0

Usage

InChI:InChI=1/C11H13N5O3/c12-10-7-11(14-3-13-10)16(4-15-7)6-1-5(2-17)8(18)9(6)19/h1,3-4,6,8-9,17-19H,2H2,(H2,12,13,14)/t6-,8-,9+/m1/s1

Upstream product

• 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 
• 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 
• 309947-86-2 N⁶,N⁶-bis(tert-butoxycarbonyl)adenine 
• 309947-84-0 tert-butyl 6-[bis(tert-butoxycarbonyl)amino]-9H-purine-9-carboxylate 
• 88559-56-2 (3aR,6aR)-2,2-dimethyl-6-[(trityloxy)methyl]-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one 
• 104010-72-2 (3aS,6aS)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one 
• 188907-70-2 (1'S,2'R,3'S,4'R)-4'-(6-chloropurin-9-yl)-1'-hydroxymethyl-1',2,'3'-trihydroxy-cyclopent-1'-ene 

Downstream Products

• 142888-03-7 C₂₇H₂₅N₅O₅ 
• 142888-07-1 C₂₇H₂₅N₅O₅ 
• 138571-54-7 6'-(R)-methylneplanocin A 
• 138662-99-4 6'-(S)-methylneplanocin A 
• 138571-53-6 N⁶-benzoyl-9<(1R,2S,3R)-4-(1-hydroxyethyl)-2,3-(isopropylidenodioxy)-4-cyclopenten-1-yl>adenine 
• 138571-49-0 N⁶-benzoyl-9-<(1R,2S,3R)-2,3-(isopropylidenedioxy)-4-(hydroxymethyl)-4-cyclopenten-1-yl>adenine 
• 138571-50-3 N⁶-benzoyl-9<(1R,2S,3R)-4-formyl-2,3-(isopropylidenedioxy)-4-cyclopenten-1-yl>adenine 
• 138571-51-4 N⁶-benzoyl-9<(1R,2S,3R)-4-ethenyl-2,3-(isopropylidenedioxy)-4-cyclopenten-1-yl>adenine 
• 78216-79-2 ara-neplanocin A 
• 88183-83-9 N⁶,6'-dibenzoylneplanocin A 2',3'-O-cyclic thiocarbonate 
• 88183-85-1 N⁶,6'-dibenzoylneplanocin A 2',3'-cyclic carbonate 
• 84207-68-1 N⁶,6'-dibenzoylneplanocin A 
• 88183-84-0 N⁶,6'-dibenzoyl-3'-deoxyneplanocin A 
• 83844-30-8 N⁶-benzoyl-9-<(1R,2S,3R)-2,3-dihydroxy-4-(hydroxymethyl)-4-cyclopenten-1-yl>adenine 

Relevant academic research and scientific papers

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

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,

Palladium-catalyzed enantioselective synthesis of carbanucleosides

A general strategy has been developed for enantioselective synthesis of diverse carbanucleosides. The key step is a Pd(0)-catalyzed enantioselective allylic amination of cis-3,5-dibenzoyloxycyclopent-2-ene 10a with the nucleobase. With guanine-derived nuc

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.

An enantio- and diastereo-controlled synthesis of (-)neplanocin A and its 2,3-di-epi isomer

An enantioselective Pd catalyzed desymmetrization of cis-3,5-dibenzoyloxycyclopent-2-ene combined with a diastereoselective epoxidation provided a common intermediate that can bifurcate to form either (-)-neplanocin A or its 2,3-di-epi isomer.

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.

3′-deoxy-3′-fluoro-xyloneplanocin A

Neplanocin A has been efficiently converted in three steps into its 3′-deoxy-3′-fluoro-xylo-analogue.

Enantiospecific Syntheses of Aristeromycin and Neplanocin A

The carbocylic nucleosides (-)-aristeromycin and (-)-neplanocin A were made enantiospecifically in nine steps and ten steps, respectively, from D-ribonic acid γ-lactone.Quenching of an organocuprate conjugate addition reaction with either acetic acid or methanesulfinyl chloride determines whether the divergent synthetic route branches toward (-)-aristeromycin or (-)-neplanocin A.An alternate synthesis of cyclopentenone 1, a common intermediate to these compounds, from D-gulonic acid γ-lactone is also described.