89291-74-7

Basic information

• Product Name: diMethyl 2-((4R,5S)-5-(2-(benzyloxy)acetyl)-2,2-diMethyl-1,3-dioxolan-4-yl)-2-oxoethylphosphonate
• Synonyms: diMethyl 2-((4R,5S)-5-(2-(benzyloxy)acetyl)-2,2-diMethyl-1,3-dioxolan-4-yl)-2-oxoethylphosphonate
• CAS NO: 89291-74-7
• Molecular Formula: C₁₈H₂₅O₈P
• Molecular Weight: 400.360061
• Mol File: 89291-74-7.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: diMethyl 2-((4R,5S)-5-(2-(benzyloxy)acetyl)-2,2-diMethyl-1,3-dioxolan-4-yl)-2-oxoethylphosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: diMethyl 2-((4R,5S)-5-(2-(benzyloxy)acetyl)-2,2-diMethyl-1,3-dioxolan-4-yl)-2-oxoethylphosphonate(89291-74-7)
• EPA Substance Registry System: diMethyl 2-((4R,5S)-5-(2-(benzyloxy)acetyl)-2,2-diMethyl-1,3-dioxolan-4-yl)-2-oxoethylphosphonate(89291-74-7)

Safety Data

• Hazardous Substances Data: 89291-74-7(Hazardous Substances Data)

Upstream product

• 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 
• 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 
• 100-39-0 benzyl bromide 
• 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 
• 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 
• 290822-88-7 (-)-1-deoxy-1-(dimethylphosphono)-3,4-O-isopropylidene-D-ribo-hexofuranose 
• 117251-95-3 Dimethyl (6-O-benzyl-1-deoxy-3,4-O-isopropylidene-β-D-ribo-hex-2-ulofuranosyl)phosphonate 
• 30725-00-9 2,3-O-isopropylidene-D-ribonic-γ-lactone 
• 89291-72-5 C₃₂H₃₅O₁₀P 

Downstream Products

• 89291-81-6 (-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>-6-chloropurine 
• 89291-82-7 (-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>adenine 
• 89291-76-9 (1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol 
• 89291-80-5 (1R,4R,5S)-(-)-1-<(5-amino-6-chloropyrimidinyl)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 
• 89291-79-2 (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 
• 72877-50-0 neplanocin A 
• 100806-47-1 (1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol p-toluenesulfonate 
• 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 
• 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 
• 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 
• 290822-97-8 (-)-9-[(1R,4R,5S)-3-(benzyloxy)methyl-4,5-dihydroxycyclopent-2-en-1-yl]-6-chloropurine 

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.

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

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