155807-20-8

Basic information

• Product Name: 3',5'-bis-O-(4-tolylsulfonyl)-2'-deoxyuridine
• CAS NO: 155807-20-8
• Molecular Weight: 536.584
• Mol File: 155807-20-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3',5'-bis-O-(4-tolylsulfonyl)-2'-deoxyuridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3',5'-bis-O-(4-tolylsulfonyl)-2'-deoxyuridine(155807-20-8)
• EPA Substance Registry System: 3',5'-bis-O-(4-tolylsulfonyl)-2'-deoxyuridine(155807-20-8)

Safety Data

• Hazardous Substances Data: 155807-20-8(Hazardous Substances Data)

Upstream product

• 4124-41-8 p-toluenesulfonylanhydride 
• 951-78-0 2'-deoxyuridine 
• 98-59-9 p-toluenesulfonyl chloride 

Relevant articles and documents

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.