28219-87-6

Upstream product

• 39686-94-7 1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 100-39-0 benzyl bromide 
• 108-24-7 acetic anhydride 

Downstream Products

• 1309453-96-0 C₅₅H₄₈O₁₆ 
• 1309453-97-1 C₆₂H₅₄O₁₆ 
• 1309453-94-8 C₅₆H₄₈O₁₃ 

Relevant academic research and scientific papers

Visible-Light-Mediated Oxidative Debenzylation Enables the Use of Benzyl Ethers as Temporary Protecting Groups

The cleavage of benzyl ethers by catalytic hydrogenolysis or Birch reduction suffers from poor functional group compatibility and limits their use as a protecting group. The visible-light-mediated debenzylation disclosed here renders benzyl ethers temporary protective groups, enabling new orthogonal protection strategies. Using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as a stoichiometric or catalytic photooxidant, benzyl ethers can be cleaved in the presence of azides, alkenes, and alkynes. The reaction time can be reduced from hours to minutes in continuous flow.

Synthesis of quercetin 3-O-β-d-apiofuranosyl-(1→2)-[α-l- rhamnopyranosyl-(1→6)]-β-d-glucopyranoside

A concise method to construct a unique 2,6-branched trisaccharide was established by regioselective glycosylation of three free hydroxyl groups on a 3-O-protected glucose moiety, and successfully used in the synthesis of quercetin 3-O-β-d-apiofuranosyl-(1→2)-[α-l-rhamnopyranosyl- (1→6)]-β-d-glucopyranoside, a flavonol O-glycoside isolated from glandless cotton seeds which showed notable antidepressant activities.