(4aR,6S,7R,8R,8aS)-6-Methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol, CAS No. 3162-96-7

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3162-96-7

Catalog No. EBD2204190

CAS 3162-96-7

Name (4aR,6S,7R,8R,8aS)-6-Methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol

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Basic Information

Synonyms: (4aR,6S,7R,8R,8aS)-6-Methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol methyl4,6-O-benzylidene-α-D-glucopyranoside Methyl4,6-O-benzylidene-alpha-D-glucopyranoside methyl4,6-O-(phenylmethylidene)-alpha-D-galactopyranoside methyl4,6-O-(phenylmethylidene)-beta-L-mannopyranoside methyl4,6-O-(phenylmethylidene)-alpha-L-mannopyranoside methyl4,6-O-(phenylmethylidene)-beta-L-glucopyranoside methyl4,6-O-(phenylmethylidene)-alpha-L-glucopyranoside

Molecular Formula: C14H18O6

Molecular Weight: 282.29

MDL Number: MFCD00006819

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

Product Description:

4,6-O-Benzylidene-α-D-glucopyranoside is a protected carbohydrate derivative. It features a benzylidene acetal group at the 4- and 6-positions of the glucose ring, which serves as a common protecting group in carbohydrate chemistry. This modification masks two hydroxyl groups simultaneously, providing regioselective protection and directing further chemical modifications to other positions on the sugar ring. This compound is primarily used as a key synthetic intermediate in the preparation of complex oligosaccharides, glycoconjugates, and modified nucleosides. Its protected structure allows for the selective functionalization of the remaining hydroxyl groups (e.g., at the 2- and 3-positions), making it a valuable building block in medicinal chemistry for the synthesis of potential drug candidates, particularly those targeting glycosidase enzymes or involved in carbohydrate-based biological recognition processes. It is a standard reagent in glycoscience research. As a specialized protected sugar, it is not a commodity chemical but a research-grade material. Handling requires standard laboratory precautions for organic compounds. Its primary value lies in its role as a precise molecular scaffold for constructing more complex, biologically relevant carbohydrate structures.

Physical Properties

Melting Point: 164-165 °C(lit.)

Boiling Point: 473 °C at 760 mmHg

Flash Point: 239.8 °C

Density: 1.36 g/cm3

Refractivity: 105 ° (C=2, MeOH)

Storage: 2-8°C

Analytical Data

Appearance: White crystalline solid