212911-13-2

Upstream product

• 212911-12-1 Benzoic acid (3aR,4R,6S,6aS)-6-tert-butoxymethyl-2-methoxy-tetrahydro-cyclopenta[1,3]dioxol-4-yl ester 
• 241806-15-5 (1aS,3aS,4R,6S)-4-benzoyloxy-(6-tert-butoxymethyl)-3a,4,5,6,6a-tetrahydrocyclopenta-1,3-dioxole-2-thione 
• 98-88-4 benzoyl chloride 
• 192118-38-0 (1R,2R,3S,4S)-4-(tert-butoxymethyl)-2,3-(isopropylidenedioxy)cyclopentan-1-ol 
• 212911-11-0 (1R,2R,3S,4S)-1-benzyloxy-2,3-dihydroxy-4-(tert-butoxymethyl)cyclopentane 
• 212911-10-9 (1R,2R,3S,4S)-1-benzoyloxy-4-(tert-butoxymethyl)-2,3-(isopropylidenedioxy)cyclopentane 

Downstream Products

• 220285-03-0 [(1R,3S)-3-(6-amino-9H-purin-9-yl)cyclopentyl]methanol 

Relevant academic research and scientific papers

Asymmetric synthesis and antiviral activities of L-carbocyclic 2',3'- didehydro-2',3'-dideoxy and 2',3'-dideoxy nucleosides

Asymmetric syntheses of L-carbocyclic 2',3'-didehydro-2',3'-dideoxy- and 2',3'-dideoxypyrimidine and purine nucleoside analogues were accomplished, and their anti-HIV and anti-HBV activities were evaluated. The key intermediate, (1S,4R)-1-benzoyloxy-4-(tert-butoxymethyl)cyclopent-2-ene (7), was prepared by benzoylation of the alcohol 2, selective deprotection of the isopropylidene group of 3, followed by thermal elimination via cyclic ortho ester or deoxygenation via cyclic thionocarbonate. The target compounds were also synthesized by thermal elimination via cyclic ortho esters from protected nucleosides. It was found that L-carbocyclic 2',3'-didehydro-2',3'- dideoxyadenosine (34) exhibited potent anti-HBV activity (EC50 = 0.9 μM) and moderate anti-HIV activity (EC50 = 2.4 μM) in vitro without cytotoxicity up to 100 μM.

Asymmetric synthesis and anti-HIV activity of L-carbocyclic 2',3'- didehydro-2',3'-dideoxyadenosine

Asymmetric synthesis of L-carbocyclic 2',3'-didehydro-2',3'- dideoxyadenosine and its analogs were accomplished and their anti-HIV activities were evaluated. It was found that L-carbocyclic 2',3'-didehydro- 2',3'-dideoxyadenosine exhibited moderately potent anti-HIV (EC50 = 2.4 μM) activity in human PBM cells without cytotoxicity up to 100 μM.