(3a'R,4S,7a'R)-2,2,2',2'-Tetramethyldihydrospiro[[1,3]dioxolane-4,6'-[1,3]dioxolo[4,5-c]pyran]-7'(4'H)-one

Name: (3a'R,4S,7a'R)-2,2,2',2'-Tetramethyldihydrospiro[[1,3]dioxolane-4,6'-[1,3]dioxolo[4,5-c]pyran]-7'(4'H)-one
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CAS No. 18422-53-2
Cat. No. CS-W016736
Purity≥98%
MDL No.MFCD00063383

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(3a'R,4S,7a'R)-2,2,2',2'-Tetramethyldihydrospiro[[1,3]dioxolane-4,6'-[1,3]dioxolo[4,5-c]pyran]-7'(4'H)-one|CS-W016736

Structure of 18422-53-2

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General Information

CAS No. 18422-53-2
Cat. No. CS-W016736
Purity ≥98%
MDL No. MFCD00063383
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₈O₆
Molecular Weight 258.27
Synonym(s) Shi Epoxidation Diketal Catalyst
SMILES O=C1[C@]2(OC(C)(OC2)C)OC[C@@]([H])(OC(C)(C)O3)[C@]13[H]

Description

This spirocyclic lactone features a rigid, electron-deficient core with four methyl groups enhancing steric shielding and solubility in polar aprotic solvents. Its bench-stable structure simplifies handling in synthetic workflows involving nucleophilic transformations or cycloadditions.

Application

(3a'R,4S,7a'R)-2,2,2',2'-Tetramethyldihydrospiro[[1,3]dioxolane-4,6'-[1,3]dioxolo[4,5-c]pyran]-7'(4'H)-one serves as a robust, bench-stable spirocyclic building block for the synthesis of complex heterocyclic scaffolds. Its rigid, fused bicyclic framework exhibits excellent functional group tolerance and facilitates stereoselective transformations in medicinal chemistry workflows. The molecule enables efficient access to diverse pyran- and dioxolane-containing motifs common in natural product analogs and API intermediates.

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-P302+P352-P304+P340

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Computational Chemistry Data

TPSA 63.22
LogP 0.585
H_Acceptors 6
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Dioxolane compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Catalysis Organocatalysts Asymmetric Organocatalysts

Key Words

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(3a'R,4S,7a'R)-2,2,2',2'-Tetramethyldihydrospiro[[1,3]dioxolane-4,6'-[1,3]dioxolo[4,5-c]pyran]-7'(4'H)-one

CAS No. 18422-53-2

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