ChemicalBook CAS DataBase List 2’,3’,5’-Tri-O-benzoyl-2-thiouridine

2’,3’,5’-Tri-O-benzoyl-2-thiouridine synthesis

5synthesis methods

Product Name:2’,3’,5’-Tri-O-benzoyl-2-thiouridine
CAS Number:21052-18-6
Molecular formula:C30H24N2O8S
Molecular Weight:572.59

141-90-2 Synthesis

141-90-2
482 suppliers
$6.00/1g

1-O-ACETYL-2,3,5-TRI-O-BENZOYL-D-RIBOFURANOSE

14215-97-5
88 suppliers
$11.00/5g

21052-18-6
19 suppliers
$95.00/50mg

Yield:21052-18-6 89%

Reaction Conditions:

Stage #1: 2-thiouracilwith ammonium sulfate;chloro-trimethyl-silane;1,1,1,3,3,3-hexamethyl-disilazane at 126; for 18 h;
Stage #2: 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranosewith tin(IV) chloride in 1,2-dichloro-ethane at 20; for 1 h;

Steps:

48 Synthesis of Compound 139

Synthesis of Compound 139. To a solution of compound 114 (24.0 g, 187.2 mmol) inhexamethyldisilazane (960 mL) were added trimethyl chlorosilane (21 .60 mL, 169.70 mmol) and thecatalytic amount of ammonium sulfate (1 .0 g, 75 mmol). The clear reaction mixture was stirred at 126cc for 1 8 h. The reaction mixture became clear, and concentrated under reduced pressure to drynessat not more than 45 °C. A solution of 1 ,2,3,5-tetra-O-acetyl-D-robofuranose (66 g, 207.60 mmol) indry 1 ,2-dichloroethane (240 mL) was added to the reaction mixture, followed by addition of tintetrachloride (28.80 mL, 249.6 mmol). The reaction mixture was stirred at room temperature for 1 h. Upon completion of the reaction as monitored by TLC, the reaction mixture was poured into saturated sodium bicarbonate (1000 mL) and stirred for 1 h. The solid was filtered off through a pad of Celite, and washed with methylene chloride. The organic phase separated, and the aqueous phase was extracted with dichioromethane. The combined organic phase was dried over anhydrous Na2SO4.The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. Thecrude product was purified by flash chromatography on a silica gel column using ethyl acetate -petroleum ether (1:2 to 1:1) resulting in compound 139 (65.0 g, 1 68.2 mmol) in 89 % yield.

References:

WO2015/196130,2015,A2 Location in patent:Page/Page column 619; 620

6974-32-9 Synthesis