89291-81-6

Basic information

• Product Name: (-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>-6-chloropurine
• Synonyms: (-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>-6-chloropurine
• CAS NO: 89291-81-6
• Molecular Weight: 412.876
• Mol File: 89291-81-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>-6-chloropurine(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>-6-chloropurine(89291-81-6)
• EPA Substance Registry System: (-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>-6-chloropurine(89291-81-6)

Safety Data

• Hazardous Substances Data: 89291-81-6(Hazardous Substances Data)

Upstream product

• 89291-72-5 C₃₂H₃₅O₁₀P 
• 89291-71-4 {2-[(4S,5R)-5-((R)-2-Benzyloxy-1-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-oxo-ethyl}-phosphonic acid dimethyl ester 
• 89291-74-7 {2-[(4S,5S)-5-(2-Benzyloxy-acetyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-oxo-ethyl}-phosphonic acid dimethyl ester 
• 117251-95-3 Dimethyl (6-O-benzyl-3,4-O-isopropylidene-α-D-ribo-2-hexulofuranosyl)phosphonate 
• 85846-80-6 5-O-benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone 
• 85846-80-6 (-)-5-O-benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone 
• 117251-95-3 (-)-6-O-benzyl-1-deoxy-1-(dimethylphosphono)-3,4-O-isopropylidene-D-ribo-hexofuranose 
• 89291-76-9 (1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol 
• 89291-78-1 (1R,4R,5S)-(-)-1-azido-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopentene 
• 89291-79-2 (1R,4R,5S)-(-)-1-amino-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopentene 
• 89291-77-0 (1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol methanesulfonate 
• 100-39-0 benzyl bromide 
• 290822-90-1 6-O-benzyl-1-deoxy-1-dimethylphosphono-3,4-O-isopropylidene-D-altrose 
• 290822-91-2 6-O-benzyl-1-deoxy-1-dimethylphosphono-3,4-O-isopropylidene-D-allose 

Downstream Products

• 290822-98-9 (1R,2S,3S,4S,5R)-(-)-1-benzyloxymethyl-4-(6-chloropurin-9-yl)-6-oxa-bicyclo[3.1.0]hexane-2,3-diol 
• 290822-99-0 (1S,2S,3S,4S,5S)-(-)-1-benzyloxymethyl-4-(6-chloropurin-9-yl)-6-oxa-bicyclo[3.1.0]hexane-2,3-diol 
• 290823-00-6 (1R,2S,3S,4S,5R)-(-)-4-(6-amino-purin-9-yl)-1-benzyloxymethyl-6-oxa-bicyclo[3.1.0]hexane-2,3-diol 
• 290823-01-7 (1S,2S,3S,4S,5S)-(-)-4-(6-amino-purin-9-yl)-1-benzyloxymethyl-6-oxa-bicyclo[3.1.0]hexane-2,3-diol 
• 72877-50-0 neplanocin A 
• 290822-97-8 (-)-9-[(1R,4R,5S)-3-(benzyloxy)methyl-4,5-dihydroxycyclopent-2-en-1-yl]-6-chloropurine 
• 89291-82-7 (-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>adenine 

Relevant articles and documents

First synthesis of (-)-neplanocin C

(-)-Neplanocin C (4), a minor component of the neplanocin family of antibiotics and a lead drug for the design of several conformationally constrained nucleosides analogues, was enantioselectively synthesized starting from D-ribono-1,4-lactone via a convergent approach in twelve steps. The proton NMR spectrum of 4 was in agreement with the corresponding natural product. Calculated coupling constants obtained from ab initio molecular modeling studies and from previously published X-ray structure of neplanocin C also corresponded to the spectroscopic data. (C) 2000 Elsevier Science Ltd.

An improved method of synthesis of neplanocin and related cyclopentenyl-containing nucleosides

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