tert-Butyl [(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

Name: tert-Butyl [(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate
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CAS No. 124752-23-4
Cat. No. CS-W022974
Purity≥95%
MDL No.MFCD02093270

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tert-Butyl [(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate|CS-W022974

Structure of 124752-23-4

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General Information

CAS No. 124752-23-4
Cat. No. CS-W022974
Purity ≥95%
MDL No. MFCD02093270
Storage -20°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₂₂O₅
Molecular Weight 258.31
Synonym(s) tert-Butyl(3R,5S)-6-oxo-3,5-O-iso-propylidene-3,5-dihydroxyhexanoate
SMILES CC(C)(C)OC(=O)C[C@H]1C[C@H](OC(C)(C)O1)C=O

Description

This tert-butyl ester features a chiral dioxane core with a formyl group at C6, enabling direct functionalization in asymmetric synthesis. The bulky tert-butyl group enhances stability and simplifies purification, while the acetal functionality supports selective protection strategies in complex molecule assembly.

Application

tert-Butyl [(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate serves as a versatile chiral building block for the synthesis of complex oxygenated scaffolds. The pendant aldehyde group enables selective transformations including reductive amination, Wittig reactions, and aldol additions. Its stable dioxane core with orthogonal protecting groups facilitates sequential functionalization, while the tert-butyl ester supports mild deprotection. This compound offers excellent bench stability and ease of purification, making it well-suited for iterative synthetic campaigns in medicinal chemistry and natural product synthesis.

Synthesis

Route1
- 124655-09-0
- ~94%
- In-stock
  
  124752-23-4
References
- Tetrahedron Letters, , vol. 31, # 18 p. 2545 - 2548
Route2
- 147489-02-9
- ~86%
- In-stock
  
  124752-23-4
References
- Tetrahedron Letters, , vol. 34, # 3 p. 513 - 516
Route3
- 79-37-8
- 124655-09-0
- ~%
- In-stock
  
  124752-23-4
References
- US4970313 A1, ;

Safety Information

Download SDS

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

Quality Control

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Computational Chemistry Data

TPSA 61.83
LogP 1.8273
H_Acceptors 5
H_Donors 0
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Aldehyde

Building Blocks Functional Group Ester

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Other aliphatic heterocycles compounds

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tert-Butyl [(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

CAS No. 124752-23-4

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