63914-08-9

Basic information

• Product Name: Thymidine, 3',5'-bis(4-methylbenzenesulfonate)
• CAS NO: 63914-08-9
• Molecular Formula: C24H26N2O9S2
• Molecular Weight: 550.61
• Mol File: 63914-08-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Thymidine, 3',5'-bis(4-methylbenzenesulfonate)(CAS DataBase Reference)
• NIST Chemistry Reference: Thymidine, 3',5'-bis(4-methylbenzenesulfonate)(63914-08-9)
• EPA Substance Registry System: Thymidine, 3',5'-bis(4-methylbenzenesulfonate)(63914-08-9)

Safety Data

• Hazardous Substances Data: 63914-08-9(Hazardous Substances Data)

Upstream product

• 6979-97-1 3',5'-diacetylthymidine 
• 452-51-7 D-2-deoxyribose 
• 4594-52-9 1,3,5-tri-O-acetyl-2-deoxyribose 
• 4124-41-8 p-toluenesulfonylanhydride 
• 50-89-5 thymidine 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 7481-90-5 3',4'-anhydrothymidine 
• 3056-17-5 stavudin 
• 26922-45-2 2,3'-anhydro-1-<2-deoxy-5-O-(p-tolylsulfonyl)-β-D-threo-pentofuranosyl>thymine 

Relevant articles and documents

SYNTHESIS AND IMPROVEMENT OF A NUCLEOSIDE ANALOGUE AS AN ANTI-CANCER AND ANTI-VIRAL DRUG

The invention is a drug for anticancer and antiviral therapy, comprising a nucleoside analogue (7) comprising a furan ring irreversibly bound to the RNA/DNA synthesis chain by phosphodiester bonds and having SP3 hybridization, and folic acid (A) bound to the nucleoside analogue (7) comprising furan ring. The synthesis method of the said nucleoside analogue is also contained within the scope of the invention. In this work, a nucleoside-analogue was transformed after converting the furan-ring hybridization from Sp2 to Sp3 to make it more selectivity with different enzymes and linking it via site 5 with the effective folic acid towards entering the substances inside the cells and to become the final compound possessing anti-cancer and anti- virus properties after controlling the replication and reproduction process in DNA.

Synthesis of Some 2',3'-Didehydro-2',3'-didepxynucleosodes Derived from Modified Pyrimidine Bases

3',5'-Bis-O-(4-tolylsulfonyl)-thymidine and 2'-deoxyuridine (13a and 13b) reacted with sodium ethoxide in boiling ethanol to give the corresponding ethoxy-oxetanes 12a and 12b in 67 and 66percent overal yield for the two-step processes starting from thymidine 4a and 2'-deoxyuridine 4b, respectively.Treatment of the ethoxy-oxetanes 12a and 12b with hydrogen sulfide and N1,N1,N3,N3-tetramethylguanidine in dry pyridine solution gave the 2-thiothymine- and 2-thiouracyl-derived oxetanes 19a and 19b in 62 and 68.5percent yield, respectively.When the latter compounds were treated with potassium tert-butoxide in dimethyl sulfoxide, the corresponding 2',3'-didehydro-2',3'-dideoxynucleosides (d4 nucleosides) 10a and 10b were obtained in 66 and 60percent yield, respectively.The 2-thiothymine-derived oxetane 19a was converted via the 5-methyl-2-thiocytosine-derived oxetane 21a into the 5-methyl-2-thiocytosine-derived d4 nucleoside 11a in 59.5percent overall yield; the 2-thiouracil-derived oxetane 19b was similarly converted into the 2-thiocytosine- and 4-N-methyl-2-thiocytosine-derived d4 nucleosides 11b and 23 in 51 and 50percent overall yield, respectively.Finally, the ethoxy-oxetane 12b was converted into the corresponding amino- and methylamino-oxetanes 25a and 25b in 74 and 83percent yield, respectively.The latter compound, 25b, was succesively converted into the 2-N-methylisocytosine-derived d4 nucleoside 26b in 62percent yield.