Allyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-1-β-D-glucopyranoside

Allyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-1-β-D-glucopyranoside

Allyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-1-β-D-glucopyranoside is a chemically modified glucopyranoside derivative. Here’s a detailed description of its structure and properties:

Chemical Structure

This compound is a complex carbohydrate derivative with several key structural features:

1. Glucopyranoside core: The base structure is a β-D-glucopyranoside, which is a sugar molecule in its cyclic form.
2. Allyl group: An allyl group (CH2=CH-CH2-) is attached at the anomeric position (C-1) in a β-configuration.
3. Benzylidene protecting group: A benzylidene group forms an acetal linkage between the 4- and 6-positions of the glucose ring, creating a rigid bicyclic structure.
4. Naphthylmethyl substituent: A 2-naphthylmethyl group is attached via an ether linkage at the 3-position of the glucose ring.

Physical Properties

While specific data for this exact compound is not provided in the search results, we can infer some properties based on similar compounds:

• Appearance: Likely a white to off-white crystalline solid
• Molecular Formula: C27H28O6 (estimated)
• Molecular Weight: Approximately 448.51 g/mol (estimated)
• Solubility: Probably soluble in organic solvents like dichloromethane, dimethylformamide, and methanol, with limited solubility in water

Chemical Properties

• Stability: The compound should be relatively stable due to the protecting groups.
• Reactivity: The allyl group at the anomeric position can participate in various chemical transformations.
• Stereochemistry: The glucopyranoside has a β-configuration at the anomeric center.

Applications

This type of compound is typically used in carbohydrate chemistry for:

1. Glycosylation reactions
2. Synthesis of complex oligosaccharides
3. Preparation of glycoconjugates
4. Studies in glycobiology and drug development

Storage and Handling

Based on similar compounds:

• Storage: Store in a cool, dry place, preferably at -20°C under inert atmosphere
• Stability: Stable under recommended storage conditions
• Incompatibilities: May be sensitive to strong oxidizing agents and moisture

Synthesis and Purification

This compound is likely synthesized through a multi-step process involving:

1. Protection of the 4,6-positions with a benzylidene group
2. Selective protection of the 3-position with a 2-naphthylmethyl group
3. Introduction of the allyl group at the anomeric position

Purification would typically involve column chromatography or recrystallization techniques.

This compound represents an advanced intermediate in carbohydrate synthesis, combining multiple protecting groups to allow for selective manipulations in complex oligosaccharide synthesis.

Citations:

1. https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4255899.htm
2. https://pubchem.ncbi.nlm.nih.gov/compound/Allyl-b-D-glucopyranoside
3. https://m.chemicalbook.com/ProductChemicalPropertiesCB4255899_EN.htm
4. https://pubchem.ncbi.nlm.nih.gov/compound/54400-75-8