(4S,4'S)-4,4'-Di((S)-sec-butyl)-4,4',5,5'-tetrahydro-2,2'-bioxazole

Name: (4S,4'S)-4,4'-Di((S)-sec-butyl)-4,4',5,5'-tetrahydro-2,2'-bioxazole
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CAS No. 133463-89-5
Cat. No. CS-0163378
Purity≥95%
MDL No.None

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(4S,4'S)-4,4'-Di((S)-sec-butyl)-4,4',5,5'-tetrahydro-2,2'-bioxazole|CS-0163378

Structure of 133463-89-5

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Description

This chiral oxazole derivative features a rigid, asymmetric backbone with sterically hindered sec-butyl groups at the 4 and 4' positions, enhancing stability and selectivity. The (4S,4'S) configuration ensures precise stereochemical control in asymmetric synthesis. Designed for use in catalytic systems and as a ligand scaffold, it delivers high enantioselectivity under mild reaction conditions.

Application

(4S,4'S)-4,4'-Di((S)-sec-butyl)-4,4',5,5'-tetrahydro-2,2'-bioxazole serves as a robust chiral auxiliary in asymmetric synthesis, enabling stereoselective C–C bond formation through well-established oxazoline-directed enolization and metalation protocols. Its bench-stable, crystalline nature and excellent functional group tolerance facilitate straightforward purification and integration into multi-step sequences. The rigid, chiral framework supports high diastereoselectivity in key transformations, making it a practical choice for the construction of complex heterocyclic scaffolds and stereochemically defined intermediates in medicinal chemistry.

General Information

CAS No. 133463-89-5
Cat. No. CS-0163378
Purity ≥95%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₂₄N₂O₂
Molecular Weight 252.35
Synonym(s) (4S,4'S)-4,4'-Di[(2S)-2-butanyl]-4,4',5,5'-tetrahydro-2,2'-bi-1,3-oxazole
SMILES CC[C@@H]([C@@H]1N=C(C2=N[C@@H]([C@@H](C)CC)CO2)OC1)C

Computational Chemistry Data

TPSA 43.18
LogP 2.6732
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 5

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-P280-P302+P352

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Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Key Words

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(4S,4'S)-4,4'-Di((S)-sec-butyl)-4,4',5,5'-tetrahydro-2,2'-bioxazole

CAS No. 133463-89-5

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