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Action of Toluene-p-thiol and Triethylamine on Fully Protected Thymidylyl-(3' -> 5')-thymidine. Possible Occurrence of Thiolate Ionpromoted Internucleotide Cleavage in the Synthesis of Oligonucleotides by the Phosphotriester Approach

DOI: 10.1039/P19810002451

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2451 - 2455 (1981)

Update date:2022-08-05

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Authors:

Reese, Colin B.Reese, Colin B.

Titmas, Richard C.Titmas, Richard C.

Valente, LydiaValente, Lydia

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Article abstract of DOI:10.1039/P19810002451

When 5'-O-methoxytetrahydropyranylthymidylyl-(3' -> 5')-3'-O-methoxytetrahydropyranylthymidine o-chlorophenyl ester (12) is treated with an excess of toluene-p-thiol and triethylamine in acetonitrile solution at room temperature, it is cleaved to give 5'-O-methoxytetrahydropyranylthymidine 3'-(o-chlorophenyl) phosphate (10) and 5'-deoxy-5'-(p-tolylthio)-3'-O-methoxytetrahydropyranylthymidine (13).The bearing of this result on the synthesis of oligonucleotides by the phosphotriester approach is discussed.

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Product name:5'-O-methoxytetrahydropyranylthymidylyl-(3'-> 5')-3'-O-methoxytetrahydropyranylthymidine o-chlorophenyl ester

Cas No:69075-24-7

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