212911-11-0

Basic information

• Product Name: (1R,2R,3S,4S)-1-benzyloxy-2,3-dihydroxy-4-(tert-butoxymethyl)cyclopentane
• Synonyms: (1R,2R,3S,4S)-1-benzyloxy-2,3-dihydroxy-4-(tert-butoxymethyl)cyclopentane
• CAS NO: 212911-11-0
• Molecular Weight: 308.375
• Mol File: 212911-11-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (1R,2R,3S,4S)-1-benzyloxy-2,3-dihydroxy-4-(tert-butoxymethyl)cyclopentane(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R,3S,4S)-1-benzyloxy-2,3-dihydroxy-4-(tert-butoxymethyl)cyclopentane(212911-11-0)
• EPA Substance Registry System: (1R,2R,3S,4S)-1-benzyloxy-2,3-dihydroxy-4-(tert-butoxymethyl)cyclopentane(212911-11-0)

Safety Data

• Hazardous Substances Data: 212911-11-0(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 192118-38-0 (1R,2R,3S,4S)-4-(tert-butoxymethyl)-2,3-(isopropylidenedioxy)cyclopentan-1-ol 

Downstream Products

• 220285-03-0 [(1R,3S)-3-(6-amino-9H-purin-9-yl)cyclopentyl]methanol 
• 212911-13-2 (1S,4R)-1-benzyloxy-4-(tert-butoxymethyl)cyclopent-2-ene 
• 241806-15-5 (1aS,3aS,4R,6S)-4-benzoyloxy-(6-tert-butoxymethyl)-3a,4,5,6,6a-tetrahydrocyclopenta-1,3-dioxole-2-thione 
• 212911-12-1 Benzoic acid (3aR,4R,6S,6aS)-6-tert-butoxymethyl-2-methoxy-tetrahydro-cyclopenta[1,3]dioxol-4-yl ester 

Relevant articles and documents

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.