[Magic Building Blocks Series 30] 1,2,3-Oxathiazolidine 2,2-dioxide building blocks_ChemScene - 코아사이언스

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Introduction

1,2,3-Oxathiazolidine 2,2-dioxide is a five-membered cyclic sulfamidate featuring an O-S-N heterocyclic backbone with a strongly electron-withdrawing SO₂ group. Its Boc-protected derivative serves as a powerful Boc-aminoethylation reagent in medicinal chemistry. The strained ring acts as an internally activated electrophile: upon nucleophilic attack, the ring opens with loss of SO₂, affording a Boc-protected aminoethyl group under mild conditions. This strategy avoids the over-alkylation and harsh reaction conditions commonly associated with conventional ethylating reagents. Moreover, this reagent enables efficient N-alkylation of challenging heterocycles, construction of piperazine/morpholine fused rings, and stereoselective introduction of chiral aminoethyl moieties using its chiral derivatives. These advantages make 1,2,3-oxathiazolidine 2,2-dioxide a valuable alkylating reagent in modern drug discovery. So far, Chemscene has developed many 1,2,3-oxathiazolidine 2,2-dioxide building blocks, with some products available in hundred-kilogram quantities.

 

1,2,3-Oxathiazolidine 2,2-dioxide building blocks

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Latest Publications Citing Use of ChemScene Products

Small 2407549, (2025).
Nat Protoc 20, 480-517 (2025).
Nat Commun 15, 10507 (2024).
Nat Commun 15, 7029 (2024).

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