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

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

Ethyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-1-thio-β-D-glucopyranoside is a chemically modified glucopyranoside derivative. Below is a detailed description based on its structure and properties:

Chemical Properties

• Molecular Formula: C29H32O5S
• Molecular Weight: 492.63 g/mol
• Appearance: White crystalline solid
• Melting Point: 113–115 °C
• Solubility: Soluble in solvents like dichloromethane (DCM), dimethylformamide (DMF), dimethyl sulfoxide (DMSO), ethyl acetate (EtOAc), and methanol (MeOH).

Structural Features

This compound is a thioglycoside derivative of glucose, featuring:

1. A benzylidene group protecting the 4,6-hydroxyl groups.
2. A 2-naphthylmethyl substituent at the 3-position.
3. A thioethyl group at the anomeric position, contributing to its β-configuration.

Applications

Such compounds are typically used in synthetic carbohydrate chemistry for:

• Glycosylation reactions.
• Serving as intermediates in the synthesis of complex oligosaccharides or glycomimetics.

Storage and Handling

• Storage Conditions: Store at 0–8 °C.
• Shipping Conditions: Ambient temperature.
• Safety: Not classified as a dangerous substance under GHS guidelines.

This compound’s unique functional groups make it useful in advanced synthetic applications, particularly in carbohydrate-based drug discovery or material science.

Citations:

1. https://synthose.com/products/EG773
2. https://pubchem.ncbi.nlm.nih.gov/compound/Ethyl-4_6-O-benzylidene-b-D-thioglucopyranoside
3. https://synthose.com/products/EG501
4. https://pmc.ncbi.nlm.nih.gov/articles/PMC3011798/
5. https://www.sigmaaldrich.com/US/en/product/combiblocksinc/comh98de4c92
6. https://www.bocsci.com/product/ethyl-3-o-2-naphthylmethyl-4-6-o-benzylidene-1-thio-d-339587.html
7. https://www.sigmaaldrich.com/US/en/substance/bbeethyl2obenzoyl3o2methylnaphthyl46obenzylidene1thiobetadglucopyranoside55668352008118
8. http://accelachem.com/cn/productview_goodsid_519661_goodscode_SY249843.html