66304-01-6

White powder

3H-1,2-Benzodithiol-3-one 1,1-dioxide is a thiosulfonate sulfur-transfer reagent for preparing oligodeoxyribonucleoside phosphorothioates by the phosphoramidite approach[1]. The reagent serves as the sulfurizing agent in automated solid-phase synthesis of sulfur-containing oligodeoxyribonucleotides, applied as a 0.5 M solution in acetonitrile for 60 s to convert phosphite triesters into phosphorothioate linkages[2-3]. It has also been used for large-scale (≥150 mmol) synthesis of phosphorothioate drugs, where its cyclic sulfoxide by-product is a potent oxidant[3].

Store at -20°C

[1] Regan, J. B., Phillips, L. R., & Beaucage, S. L. (1992). LARGE-SCALE PREPARATION OF THE SULFUR-TRANSFER REAGENT 3H-1,2-BENZODITHIOL-3-ONE 1,1-DIOXIDE. Organic Preparations and Procedures International, 24(4), 488–492. https://doi.org/10.1080/00304949209356233
[2] Zhou, Y., Zhang, B., Dong, J., Li, J., Yang, S., Ye, L. (2022). Assembly of Benzo[ c ][1,2]dithiol-3-ones via Acid-Promoted Denitrogenative Transannulation of Benzotriazinones. Organic Letters, 24(49), 9012–9016. https://doi.org/10.1021/acs.orglett.2c03638
[3] Cheruvallath, Z. S., Carty, R. L., Moore, M. N., Capaldi, D. C., Krotz, A. H., Wheeler, P. D., Turney, B. J., Craig, S. R., Gaus, H. J., Scozzari, A. N., Cole, D. L., Ravikumar, V. T. (1999). Synthesis of Antisense Oligonucleotides:  Replacement of 3H-1,2-Benzodithiol-3-one 1,1-Dioxide (Beaucage Reagent) with Phenylacetyl Disulfide (PADS) As Efficient Sulfurization Reagent:  From Bench to Bulk Manufacture of Active Pharmaceutical Ingredient. Organic Process Research & Development, 4(3), 199–204. https://doi.org/10.1021/op990077b