α-D-Ribofuranose, 1,3,5-tribenzoate
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α-D-Ribofuranose, 1,3,5-tribenzoate
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CAS No:
22224-41-5
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Formula:
C26H22O8
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Chemical Name:
α-D-Ribofuranose, 1,3,5-tribenzoate
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Synonyms:
α-D-Ribofuranose,1,3,5-tribenzoate;Ribofuranose,1,3,5-tribenzoate;1,3,5-Tri-O-benzoyl-α-D-ribofuranose;α-D-1,3,5-Tri-O-benzoyl-ribofuranose
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CAS No:
Characteristics
108.36000
3.01180
Pale brown Powder
1.4±0.1 g/cm3
139-142 °C @ Solvent: Dichloromethane, Diethyl ether
629.6°C at 760 mmHg
213.0±25.0 °C
1.633
Insoluble in water, easily soluble in chloroform.
1.02E-16mmHg at 25°C
α-D-Ribofuranose, 1,3,5-tribenzoate Use and Manufacturing
The synthesis of compound vi: The compound v (2.57mmol) was dissolved in 26 ml dry dichloromethane and dry HCl gas was slowly introduced into an ice-water bath for 2.5 hours. The solution was washed with 19.5ml ice water and the organic layer was separated. The organic layer was washed with saturated sodium bicarbonate until the water layer shows weak alkaline, and then washed with ice water until the water layer shows neutral, dried over anhydrous sodium sulfate for more than 4 hours, and then drawn off under a reduced pressure to obtain light yellow syrup. The syrup was recrystallized using the mixed solvent of hexane and dichloromethane, so as to obtain the white solid compound vi (65.1percent). To a ice-cooled solution of 1, 3, 5-tri-O-benzoyl-alpha-d-ribofuranose (4) (0.50g, 1.08mmol) in anhydrous pyridine (10mL) was added benzoyl chloride (0.25mL, 2.15mmol) and the mixture was stirred for 20hat room temperature. After standard workup the obtained residue was applied to a chromatographic column (silica gel, 60cm3) and eluted with a linear ethyl acetate gradient (20'30% v/v, 300mL) in hexane. The fractions containing the product were collected and evaporation to yield 0.58g (95%) of 6 as colorless oil. 6: similarly 4.2.1.
Used as an intermediate for the drug crolabine
Computed Properties
Molecular Weight:462.4
XLogP3:4.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:10
Exact Mass:462.13146766
Monoisotopic Mass:462.13146766
Topological Polar Surface Area:108
Heavy Atom Count:34
Complexity:691
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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α-D-Ribofuranose, 1,3,5-tribenzoate
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