(R)-tert-Butyl 4-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide

Name: (R)-tert-Butyl 4-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide
Brand: ChemScene
Availability: InStock
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CAS No. 454248-53-4
Cat. No. CS-0053088
Molecule weight237.27
Purity≥96%
MDL No.None

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(R)-tert-Butyl 4-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide|CS-0053088

Structure of 454248-53-4

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General Information

CAS No. 454248-53-4
Cat. No. CS-0053088
Purity ≥96%
MDL No. None
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₁₅NO₅S
Molecular Weight 237.27
Synonym(s) Tert-butyl (R)-4-methyl-2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylate
SMILES C[C@@H]1COS(=O)(=O)N1C(=O)OC(C)(C)C

Description

(R)-tert-Butyl 4-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide features a chiral oxathiazolidine scaffold with a bench-stable sulfone moiety and a sterically protected tert-butyl ester. This configuration delivers high diastereoselectivity in asymmetric synthesis, enabling efficient incorporation of sulfur-containing motifs into complex molecular architectures under mild conditions.

Application

(R)-tert-Butyl 4-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide serves as a stable, bench-ready chiral synthon for sulfur-containing heterocycles. Its sulfonamide-like reactivity enables efficient nucleophilic displacement and transition-metal-catalyzed transformations. The oxathiazolidine core provides excellent functional group tolerance and facilitates stereoselective C–X bond formation, making it valuable in the synthesis of complex intermediates for medicinal chemistry and catalytic process development.

Synthesis

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  454248-53-4
References
- Posakony, J. J.; Tewson, T. J. Journal of Labelled Compounds and Radiopharmaceuticals, 2001 , vol. 44, p. S925 - S926

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 72.91
LogP 0.887
H_Acceptors 5
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Other aliphatic heterocycles compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Key Words

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(R)-tert-Butyl 4-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide

CAS No. 454248-53-4

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