tert-Butyl 1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide

Name: tert-Butyl 1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide
Brand: ChemScene
Availability: InStock
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CAS No. 459817-82-4
Cat. No. CS-0084737
Purity≥95%
MDL No.MFCD20527196

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tert-Butyl 1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide|CS-0084737

Structure of 459817-82-4

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General Information

CAS No. 459817-82-4
Cat. No. CS-0084737
Purity ≥95%
MDL No. MFCD20527196
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₁₃NO₅S
Molecular Weight 223.25
Synonym(s) 1,2,3-oxathiazolidine-3-carboxylic acid, 1,1-dimethylethyl ester, 2,2-dioxide
SMILES O=C(N1S(OCC1)(=O)=O)OC(C)(C)C

Description

tert-Butyl 1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide is a bench-stable, moisture-tolerant sulfonamide equivalent featuring a rigid oxathiazolidine scaffold. This stable chiral building block integrates seamlessly into asymmetric synthesis workflows, enabling efficient access to sulfur-containing heterocycles and peptide mimetics through controlled reductive cleavage.

Application

tert-Butyl 1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide serves as a stable, bench-ready chiral synthon for sulfur-containing heterocycles. It functions as a versatile building block in asymmetric synthesis, enabling efficient access to sulfonamide and sulfonylamine derivatives via controlled ring opening. Its robust stability under standard reaction conditions facilitates straightforward purification and broad functional group tolerance, making it well-suited for iterative synthetic sequences in medicinal chemistry and process development.

Synthesis

Route1
- In-stock
  
  26690-80-2
- ~87%
- In-stock
  
  459817-82-4
References
- Mansueto, Markus; Frey, Wolfgang; Laschat, Sabine Chemistry - A European Journal, 2013 , vol. 19, # 47 p. 16058 - 16065
Route2
- In-stock
  
  24424-99-5
- ~%
- In-stock
  
  459817-82-4
References
- Das, Biswanath; Reddy, Cheruku Ravindra; Nagendra, Siddavatam; Lingaiah, Maram Tetrahedron Letters, 2011 , vol. 52, # 27 p. 3496 - 3498

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07,GHS09
Signal Word : Warning	UN#: 3077
Class : 9	Packing Group : Ⅲ
Hazard Statements : H302-H410
Precautionary Statements : P264-P270-P273-P330-P391-P501

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Computational Chemistry Data

TPSA 72.91
LogP 0.4985
H_Acceptors 5
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Other aliphatic heterocycles compounds

Key Words

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tert-Butyl 1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide

CAS No. 459817-82-4

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