1,2:4,5-di-O-isopropylidene-β-D-erythro-hexo-2,3-diulo-2,6-pyranose

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Cat Number

INT18422532

CAS Number

18422-53-2

For research use only. We do not supply to patients.

For pharmaceutical-grade products or other inquiries, please contact our experts.

Product Detail Description Customer Q&A

CAS Number

18422-53-2

Storage

2-8℃

Synonyms

di-O-isopropylidene-beta-D-erythro-2,3-hexodiulopyranose

Molecular Formula

C12H18O6

Molecular Weight

258.27

Smiles

C12(COC(C)(C)O1)OCC1OC(C)(C)OC1C2=O

Appearance

White to pale yellow powder

Melting Point

102-104℃

Boiling Point

341.9℃

Relative Density

1.28

General Description

1,2:4,5-di-O-isopropylidene-β-D-erythro-hexo-2,3-diulo-2,6-pyranose (also known as diacetone fructose or 1,2:4,5-di-O-isopropylidene-α-D-erythro-2,3-hexodiulo-2,6-pyranose) is a fully protected derivative of a six-carbon keto-sugar featuring two isopropylidene (acetonide) protecting groups and a diketo functionality at the C-2 and C-3 positions of the pyranose ring. This compound is a versatile chiral building block derived from D-fructose, providing multiple stereocenters and protected functional groups for asymmetric synthesis.

Mechanism of Action

1,2:4,5-di-O-isopropylidene-β-D-erythro-hexo-2,3-diulo-2,6-pyranose functions as a chiral, enantiomerically pure carbohydrate-derived building block in asymmetric synthesis. The isopropylidene groups are stable under neutral and basic conditions but removed under acidic aqueous conditions, enabling selective deprotection. The C-2 and C-3 diketo functionality can undergo regioselective reduction, nucleophilic addition, and cyclocondensation reactions. The bicyclic acetal (1,2-O-isopropylidene) protects the 1,2-diol of the parent sugar.

Application

1,2:4,5-di-O-isopropylidene-β-D-erythro-hexo-2,3-diulo-2,6-pyranose is used as a chiral auxiliary and intermediate in asymmetric synthesis of pharmaceuticals, including the synthesis of nucleoside analogs, polyketide derivatives, and chiral ligands. It serves as a starting material in the synthesis of natural products and chiral drugs where stereochemistry is critical for biological activity. The fructose-derived diacetonide is also used in the synthesis of sweeteners and flavor compounds.

What is the recommended storage condition for 1,2:4,5-di-O-isopropylidene-β-D-erythro-hexo-2,3-diulo-2,6-pyranose?

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.

What documentation is provided with each batch of 1,2:4,5-di-O-isopropylidene-β-D-erythro-hexo-2,3-diulo-2,6-pyranose?

Each batch is accompanied by a Certificate of Analysis (COA) covering identity, potency, and relevant purity tests. Safety Data Sheets (SDS) are available upon request.

What is the primary synthetic application of 1,2:4,5-di-O-isopropylidene-β-D-erythro-hexo-2,3-diulo-2,6-pyranose?

It is widely used as a key building block or intermediate in multi-step pharmaceutical synthesis workflows, providing versatile reactivity for constructing target molecular architectures.

What scale of supply is available for 1,2:4,5-di-O-isopropylidene-β-D-erythro-hexo-2,3-diulo-2,6-pyranose for pilot or commercial synthesis?

Supply is available from laboratory research scale through multi-kilogram pilot quantities. Commercial-scale supply can be discussed based on projected demand.

What is the minimum order quantity (MOQ) for 1,2:4,5-di-O-isopropylidene-β-D-erythro-hexo-2,3-diulo-2,6-pyranose?

Flexible MOQ options are available to support both early-stage research and large-scale manufacturing needs. Our team can tailor order quantities to match your specific requirements.