diacetone D-mannose, CAS No. 14131-84-1

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14131-84-1

Catalog No. EBD2203516

CAS 14131-84-1

Name diacetone D-mannose

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Basic Information

Synonyms: 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose diacetoneD-mannose Diaceton-alpha-D-mannofuranose DIACETONE-D-MANNOSE 2,3:5,6-DI-O-ISOPROPYLIDENE-A-D-MANNOFURANOSE 2,3:5,6-DI-O-ISOPROPYLIDENE-A-D-MANNOPYRANOSE (+)-2,3:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-MANNOFURANOSE 2,3,5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-MANNOFURANOSE 6-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol(non-preferredname) (3aS,4S,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol(non-preferredname) Diaceton-D-Mannofuranose

Molecular Formula: C12H20O6

Molecular Weight: 260.28

MDL Number: MFCD00134206

Categories: Medicinal Chemistry > Biochemicals and Life Science Reagents > Saccharides, Nucleosides, and Nucleotides Synthetic Chemistry > Organic Building Blocks > Other Organic Building Blocks

Product Description:

Diacetone-D-mannose is a protected derivative of D-mannose, specifically the 2,3:5,6-di-O-isopropylidene acetal. This compound is a white to off-white crystalline powder. The isopropylidene protecting groups render the sugar ring less polar and more soluble in organic solvents, making it a crucial intermediate in synthetic carbohydrate chemistry. Its primary application is as a key chiral building block in the synthesis of complex carbohydrates, nucleosides, and glycoconjugates. It serves as a versatile precursor for the preparation of various D-mannose derivatives, C-glycosides, and iminosugars, which are important in medicinal chemistry and drug discovery. Compounds derived from diacetone-D-mannose are investigated for their biological activities, including as glycosidase inhibitors and potential therapeutics. As a protected sugar, it is a fundamental reagent in the toolbox of synthetic organic and medicinal chemists working on carbohydrate-based drugs, vaccine adjuvants, and probes for glycolbiology studies. Its stability and handleability make it a preferred starting material over the parent, more labile D-mannose for multi-step syntheses.

Physical Properties

Melting Point: 125-126 °C (dec.)(lit.)

Boiling Point: 359.3 °C at 760 mmHg

Flash Point: 171.1 °C

Density: 1.214 g/cm3

Analytical Data

Appearance: white to light yellow crystal powder