1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose, CAS No. 2595-05-3

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2595-05-3

Catalog No. EBD2198554

CAS 2595-05-3

Name 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose

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Basic Information

Synonyms: 1,2:5,6-di-o-isopropylidene-d-allofuranose 1,2:5,6-di-o-isopropylidene-a-d-allofuranose 1,2,5,6-di-o-isopropylidene-alpha-d-allofuranose 1,2:5,6-di-o-isopropylidene-alpha-d-allofuranoside diacetone-alpha-d-all 5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol diisopropylideneallofuranose α-D-Allofuranose,1,2:5,6-bis-O-(1-methylethylidene)- 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose (3aR,5S,6R,6aR)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[4,5-d][1,3]dioxol-6-ol (3aR,5S,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol(non-preferredname) 5,6-Di-O-isopropylidene-a-D-allofuranose diacetone-d-allo

Molecular Formula: C12H20O6

Molecular Weight: 260.28

MDL Number: MFCD00135634

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

Product Description:

1,2:5,6-Di-O-isopropylidene-α-D-allofuranose is a protected derivative of the sugar D-allose. It is a white to off-white crystalline powder with a molecular formula of C12H20O6. This compound is characterized by the presence of two isopropylidene (acetonide) protecting groups, which mask the hydroxyl groups at the 1,2 and 5,6 positions of the allofuranose ring, rendering it a stable and versatile synthetic intermediate. Its primary application is in carbohydrate chemistry and medicinal chemistry as a crucial chiral building block. The protected structure makes it a valuable starting material for the synthesis of more complex carbohydrates, nucleosides, and glycomimetics. It is extensively used in the preparation of various biologically active molecules, including potential antiviral agents and other pharmaceuticals that require specific sugar scaffolds. The compound serves as a precursor to other protected sugars and is a common reagent in the synthesis of modified nucleosides. While its main utility lies in life science research and drug discovery as a specialized intermediate, its defined structure and role as a starting material also position it within the broader category of organic synthesis building blocks for constructing complex molecular architectures.

Physical Properties

Melting Point: 73-76 °C(lit.)

Boiling Point: 362.753 °C at 760 mmHg

Flash Point: 173.187 °C

Density: 1.214 g/cm3

Refractivity: 36.5 ° (C=1, CHCl3)

Storage: 2-8°C