117251-95-3

Upstream product

• 30725-00-9 2,3-O-isopropylidene-D-ribonic-γ-lactone 
• 100-39-0 benzyl bromide 
• 290822-88-7 (-)-1-deoxy-1-(dimethylphosphono)-3,4-O-isopropylidene-D-ribo-hexofuranose 
• 85846-80-6 5-O-benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone 
• 756-79-6 dimethyl methane phosphonate 
• 85846-80-6 (-)-5-O-benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone 
• 34939-91-8 dimethyl lithiomethylphosphonate 

Downstream Products

• 89291-72-5 C₃₂H₃₅O₁₀P 
• 72877-50-0 neplanocin A 
• 89291-77-0 (1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol methanesulfonate 
• 89291-79-2 (1R,4R,5S)-(-)-1-amino-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopentene 
• 89291-78-1 (1R,4R,5S)-(-)-1-azido-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopentene 
• 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 
• 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 
• 89291-80-5 (1R,4R,5S)-(-)-1-<(5-amino-6-chloropyrimidinyl)amino>-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopentene 
• 89291-76-9 (1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol 
• 117307-62-7 (3aR,6aR)-6-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-one 
• 89291-82-7 (-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>adenine 
• 89291-81-6 (-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>-6-chloropurine 
• 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 
• 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 

Relevant academic research and scientific papers

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.

Chiral pool synthesis of 4a-substituted carbocyclic cyclopentanoid nucleoside precursors, I

A suitable protected D-ribono-1,4-lactone derivative has been used for the straightforward chiral pool synthesis of cyclopentanoid nucleoside precursors. Thus, epoxidation followed by deoxygenation or regioselective ring opening led to nucleoside precurso

CONVENIENT OXIDATIONS OF CARBOHYDRATE DERIVED LACTOLS AND OF ε-HYDROXY-β-KETOPHOSPHONATES

Convenient oxidation of carbohydrate derived lactols to lactones as well as the oxidation of ε-hydroxy-β-ketophosphonates to their corresponding β,ε-diketophosphonates can be performed with the Dess-Martin periodinane in high yields.

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.