ChemicalBook CAS DataBase List 2',2'-Difluoro-2'-deoxycytidine-3',5'-dibenzoate

2',2'-Difluoro-2'-deoxycytidine-3',5'-dibenzoate synthesis

5synthesis methods

Product Name:2',2'-Difluoro-2'-deoxycytidine-3',5'-dibenzoate
CAS Number:134790-39-9
Molecular formula:C23H19F2N3O6
Molecular Weight:471.41

2-Deoxy-2,2-difluoro-D-ribofuranose-3,5-dibenzoate-1-methanesulfonate

134877-42-2
132 suppliers
$45.00/25mg

18037-10-0 Synthesis

N-(Trimethylsilyl)-2-[(trimethylsilyl)oxy]pyrimidin-4-amine

18037-10-0
74 suppliers
$51.00/100 mg

2',2'-Difluoro-2'-deoxycytidine-3',5'-dibenzoate

134790-39-9
205 suppliers
$117.00/2g

Yield:134790-39-9 85.5%

Reaction Conditions:

at 120; for 3 h;Heating;

Steps:

10 Example 10
Cytosine (24.4 g, 0.22 mol),Hexamethyldisilazane (46.2 mL, 0.22 mol)And ammonium sulfate (0.03g) in 2L three-necked flask and mix well,After heating to reflux to clarify the reaction,Continue incubation reaction 30min.Cooled to below 80 ,The solvent was distilled off under reduced pressure,Precipitation of solids.Me3SiOTf (48.9 g, 0.22 mol)Anisole (400 ml),Heat and stir to dissolve the solid.The reaction solution was addedα-2-deoxy-2,2-difluoro-D-ribofuranosyl-3,5-bisbenzoate-1-methanesulfonate(90.0 g, 0.20 mol, β-isomer content 0.07%),Anisole (200 ml) was added thereto,120 reaction 3h,TLC detection reaction was completed,After cooling to room temperature diluted with ethyl acetate (500 ml)Stirring,4M hydrochloric acid (300 mL) was added dropwise,After warming to 70 insulation 2h.Filtered while still hotFilter cake and then in 70 water beating 1h,Filtered while still hotThe filter cake was suspended in water (300 mL) and adjusted to pH 7 with 5% sodium bicarbonate solution,filter,After drying under vacuum, 80.6 g of 2'-deoxy-2 ', 2'-difluorocytidine-3', 5'-dibenzoate was obtained,Isomer content 0.08%Yield 85.5%.

References:

Lianyungang Hengyun Pharmaceutical Technology Co., Ltd.;Zhang Qingjie;Chen Zhifeng CN106478747, 2017, A Location in patent:Paragraph 0058; 0059; 0060

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