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3-O-Benzyl-1,2-O-isopropylidene-α-D-glucofuranose is a protected glucose derivative used as a key building block in organic synthesis, especially for complex carbohydrates and nucleosides.
Core Structure: α-D-Glucose locked in a 5-membered furanose ring (unstable in free glucose).
Protecting Groups:
1,2-O-Isopropylidene: Acetal protecting C1-OH and C2-OH, stabilizing the furanose form.
3-O-Benzyl: Ether protecting C3-OH (benzyl group, removable later).
Function: Enables selective chemical reactions at the remaining free hydroxyl (C6-OH) or the anomeric center after deprotection. Widely used to synthesize modified sugars, nucleoside analogs (drugs), and glycoconjugates.
Form: Typically a white crystalline solid.
3-O-Benzyl-1,2-O-isopropylidene-α-D-glucofuranose is a protected derivative of glucose used as a key synthetic intermediate in carbohydrate and nucleoside chemistry.
Key Features:
Core Structure: α-D-Glucose locked in a 5-membered furanose ring (not the typical pyranose).
Protecting Groups:
1,2-O-Isopropylidene: Acetal group protecting the anomeric (C1) and C2 hydroxyls, stabilizing the furanose form.
3-O-Benzyl: Benzyl ether group protecting the C3 hydroxyl, allowing selective manipulation at C5/C6 later.
Function: Serves as a versatile building block for synthesizing:
Modified sugars (e.g., rare deoxy sugars)
Nucleoside analogs (antiviral/anticancer drugs)
Glycoconjugates (oligosaccharides, glycopeptides).
Properties: Typically a white crystalline solid, soluble in organic solvents (e.g., CH₂Cl₂, THF).
Purpose: Its strategic protection enables controlled, stepwise chemical reactions on glucose, crucial for constructing complex bioactive molecules.
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