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[ CAS No. 14215-97-5 ] {[proInfo.proName]}

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Chemical Structure| 14215-97-5
Chemical Structure| 14215-97-5
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Product Details of [ 14215-97-5 ]

CAS No. :14215-97-5 MDL No. :MFCD00067634
Formula : C28H24O9 Boiling Point : -
Linear Structure Formula :- InChI Key :GCZABPLTDYVJMP-ASAMFVBJSA-N
M.W : 504.48 Pubchem ID :10929242
Synonyms :
Chemical Name :(3R,4R,5R)-2-Acetoxy-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate

Safety of [ 14215-97-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 14215-97-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 14215-97-5 ]

[ 14215-97-5 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 6974-32-9 ]
  • [ 555-30-6 ]
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  • 2
  • [ 149765-16-2 ]
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  • [ 873792-67-7 ]
  • 3
  • [ 124-41-4 ]
  • [ 149765-16-2 ]
  • [ 14215-97-5 ]
  • [ 480439-92-7 ]
  • 4
  • [ 100644-67-5 ]
  • [ 14215-97-5 ]
  • 6-amino-4-methoxy-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1H-pyrazolo[3,4-d]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% A suspension of 6-amino-4-methoxy-1H-pyrazolo[3.4-d]pyrimidine (purine base A, 9.0g, 54.5 mmol, 1.0 eq) and a catalytic amount of ammonium sulfate in hexamethyldisilazane(HMDS, 150 mL) was refluxed for 6 h. The excess hexamethyldisilazane was removed byevaporation under reduced pressure, and the residue was dissolved in 1,2-dichloroethane (200 mL).l-O-Acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose (ribose I) (35.7 g, 70.8 mmol, 1.3 eq) was added at roomtemperature. The reaction mixture was cooled to 0 C, and trimethylsilyl trifluoromethanesulfonate(TMSOTf, 29.6 mL, 163.5 mmol, 3.0 eq) was added dropwise for 30 min with stirring. The reactionmixture was stirred at room temperature overnight. Upon completion of the reaction as monitoredby TLC, the mixture was diluted with dichloromethane (200 mL) and washed with saturated sodiumbicarbonate solution. The aqueous layer was extracted with dichloromethane. The combinedorganic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure.The resulting residue was purified by column chromatography to afford 10.0 g main product N9-isomer 24 as a white solid in 30.3% yield with an HPLC purity of 96%; Rf = 0.3 (petroleum ether±ethylacetate = 1:1).
  • 5
  • [ 100644-67-5 ]
  • [ 14215-97-5 ]
  • 6-amino-4-methoxy-2-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2H-pyrazolo[3,4-d]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
83.3% With boron trifluoride diethyl etherate; In acetonitrile; at 95℃; for 0.25h; 6-Amino-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine (purine base A; 8.0 g, 48.4 mmol, 1.0 eq) wassuspended in 200 mL dry acetonitrile and 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose (ribose I) (36.6g, 72.6 mmol, 1.5 eq) was added. The reaction mixture was heated to reflux at 95 C, and the freshlydistilled BF3OEt2 (12.2 mL, 96.8 mmol, 2.0 eq) was then added with stirring. The reaction mixturebecame clear immediately and then slowly became dark. The mixture was stirred at this temperaturefor 15 min. Upon the completion of the reaction as monitored by TLC, the reaction mixture was cooledto room temperature and concentrated under reduced pressure. The resulting residue was purified bycolumn chromatography to afford 25.0 g N8-product 25 as a white solid in 83.3% yield with an HPLCpurity of 96.8%. Rf = 0.6 (dichloromethane-methanol = 30:1). UV-vis (MeOH) lmax: 225 nm; ESI-MSm/z: 610.6 [M + H]+.
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