ChemicalBook CAS DataBase List 2,6-Dichloro-9-(2-C-Methyl-2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)purine

2,6-Dichloro-9-(2-C-Methyl-2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)purine synthesis

5synthesis methods

Product Name:2,6-Dichloro-9-(2-C-Methyl-2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)purine
CAS Number:205171-10-4
Molecular formula:C32H24Cl2N4O7
Molecular Weight:647.46

5451-40-1 Synthesis

5451-40-1
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$10.00/1g

15397-15-6 Synthesis

1,2,3,5-Tetra-O-benzoyl-2-C-methyl-beta-D-ribofuranose

15397-15-6
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2,6-Dichloro-9-(2-C-Methyl-2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)purine

205171-10-4
18 suppliers
$1066.00/1g

Yield:205171-10-4 97%

Reaction Conditions:

with trimethylsilyl trifluoromethanesulfonate;1,8-diazabicyclo[5.4.0]undec-7-ene in acetonitrile at 0 - 65; for 5.33 h;

Steps:

73.a

Step a: To β-D-ribofuranose, 2-C-methyl-, 1,2,3,5-tetrabenzoate (4.0 g, 6.89 mmol, 1 equiv.) and 2,6-dichloropurine (1.43 g, 7.58 mmol, 1.1 equiv.) in acetonitrile (23 mL) at 0 °C was added 1,8-Diazabicyclo[5.4.0]undec-7-ene (2.58 mL, 17.23 mmol, 2.5 equiv.) followed by trimethylsilyl trifluoromethanesulfonate (5.11 mL, 28.25 mmol, 4.1 equiv.) dropwise over 5 minutes. The reaction mixture was stirred at 0 °C for 15 minutes and heated at 65 °C for 5 hours. After cooling to room temperature the reaction was diluted with dichloromethane, washed with sat. aq. sodium bicarbonate (x2), and brine (x1). The organics were dried over MgSO₄, filtered and concentrated under reduced pressure. The desired product was obtained following column chromatography (SiO₂, 25% to 66% EtOAc/Hexane) as a white solid (1.30 g, 97%).

References:

WO2017/120508,2017,A1 Location in patent:Paragraph 0289

15397-15-6 Synthesis

15397-15-6
133 suppliers
$18.00/1g

5451-40-1 Synthesis

5451-40-1
484 suppliers
$10.00/1g

205171-10-4
18 suppliers
$1066.00/1g

References

98-88-4 Synthesis