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

Name: tert-Butyl (S)-4-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide
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CAS No. 439948-91-1
Cat. No. CS-0048512
Purity≥97%
MDL No.None

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tert-Butyl (S)-4-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide|CS-0048512

Structure of 439948-91-1

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General Information

CAS No. 439948-91-1
Cat. No. CS-0048512
Purity ≥97%
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(4S)-4-methyl-2,2-dioxo-1,2λ,3-oxathiazolidine-3-carboxylate
SMILES C[C@H]1COS(=O)(=O)N1C(=O)OC(C)(C)C

Description

This chiral sulfone scaffold features a bench-stable, moisture-tolerant oxathiazolidine core with defined stereochemistry at the 4-methyl position. The tert-butyl ester group enables straightforward deprotection under mild acidic conditions, while the sulfonyl moiety enhances solubility and stability. This configuration facilitates direct incorporation into peptide mimetics and constrained heterocyclic libraries via robust coupling protocols.

Application

tert-Butyl (S)-4-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide serves as a stable, bench-ready chiral building block for the synthesis of sulfur-containing heterocycles and peptidomimetics. Its oxathiazolidine core enables selective transformations under mild conditions, with excellent functional group tolerance and straightforward deprotection. The tert-butyl ester facilitates purification and isolation, while the stereochemistry is retained during key coupling steps, making it ideal for applications in medicinal chemistry and catalytic asymmetric synthesis.

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 : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362-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 Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Other aliphatic heterocycles compounds

Key Words

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

CAS No. 439948-91-1

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