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

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.

Total Synthesis of (-)-Neplanocin A

An efficient synthesis of neplanocin A, which is easily adaptable for the preparation of other cyclopentenyl containing nucleoside isosteres, has been developed.This enantioselective synthesis provides control of two of the three chiral centers of neplano

TOTAL SYNTHESIS OF (-)-NEPLANOCIN A

A total synthesis of (-)-neplanocin A has been accomplished in 15 steps starting from the readily available D-(+)-ribonic acid γ-lactone.