4,4-dimethyl-3,5,8-trioxabicyclo[5.1.0]octane

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Cat Number

INT57280225

CAS Number

57280-22-5

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Product Detail Description Customer Q&A

CAS Number

57280-22-5

EINECS

421-750-9

Storage

2-8℃

Synonyms

3,5,8-Trioxabicyclo[5.1.0]octane, 4,4-diMethyl-;4,4-diMethyl-3,5,8-trioxabicyclo[5.1.0]octane

Molecular Formula

C7H12O3

Molecular Weight

144.17

Smiles

C12C(O1)COC(C)(C)OC2

Appearance

Clear colorless to yellow liquid

Boiling Point

179℃

Relative Density

1.07

General Description

4,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane is a complex bicyclic acetal featuring two fused rings (a bicyclo[5.1.0]octane skeleton) with three oxygen atoms incorporated into the ring system (3,5,8-trioxa) and two gem-dimethyl groups at the C-4 bridgehead position. The bicyclic acetal structure is formed by the condensation of pentaerythritol with acetaldehyde or formaldehyde, creating a rigid, polyether-like scaffold that resists metabolic cleavage.

Mechanism of Action

4,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane functions as a protected polyol building block and as a scaffold in the synthesis of crown ether analogs and cryptand derivatives. The gem-dimethyl groups create steric bulk and hydrophobic shielding around the acetal oxygen atoms, which can coordinate to metal ions. The rigid bicyclic structure constrains molecular geometry and can serve as a conformational lock in drug molecules.

Application

4,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane is used as a key intermediate in the synthesis of macrocyclic compounds, crown ether analogs, and heterocyclic systems. The trioxabicyclo[5.1.0]octane scaffold is found in certain prostaglandin analogs and in peptide cyclization reagents. It is also used as a precursor in the synthesis of tripodal ligands for coordination chemistry and metal-catalyzed asymmetric transformations.

What is the recommended storage condition for 4,4-dimethyl-3,5,8-trioxabicyclo[5.1.0]octane?

It should be stored at 2-8°C in a well-sealed container, protected from moisture and direct light, to maintain its chemical integrity throughout the shelf life.

Is a Certificate of Analysis (COA) available for 4,4-dimethyl-3,5,8-trioxabicyclo[5.1.0]octane?

Yes, a fully verified COA is issued for every batch and can be shared electronically. Additional documentation such as MSDS or impurity profiles may be requested separately.

Can 4,4-dimethyl-3,5,8-trioxabicyclo[5.1.0]octane be provided with custom specifications for synthetic applications?

Custom specifications including adjusted particle size, solvent residue limits, or additional purity testing can be arranged for qualified customers with defined requirements.

Is 4,4-dimethyl-3,5,8-trioxabicyclo[5.1.0]octane available in high-chemical-purity grade for pharmaceutical synthesis?

Yes, it is supplied in high chemical purity grades suitable for demanding pharmaceutical intermediate applications. Specifications and analytical data are available upon request.

What quality standards govern the production of 4,4-dimethyl-3,5,8-trioxabicyclo[5.1.0]octane?

Production is carried out under GMP-aligned quality systems with full traceability and documented quality controls for each manufacturing run.