2,2-Dichloro-1,3-benzodioxole as a Hydroxyl Protection Reagent for Carbohydrate Compounds

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 6, 2025

The application of 2,2-dichloro-1,3-benzodioxole (DCBZ) as a versatile hydroxyl protection reagent in carbohydrate chemistry has been demonstrated. DCBZ exhibited high reactivity with diverse vicinal and remote dihydroxyl groups furanoses pyranoses to form benzodioxole (BZDO)-protected products. BZDO group showed remarkable stability under basic, redox, glycosylation conditions can be efficiently removed acid the presence diol, highlighting its utility orthogonal synthesis complex glycans.

Language: Английский

Ph₃PO-Modulated Kdo Glycosidation for Stereoselective Synthesis of β-Kdo-Containing Disaccharides

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 30, 2024

A Ph3PO-modulated β-selective Kdo glycosidation approach is developed for the stereoselective synthesis of β-Kdo glycosides. With readily available per-O-acetylated ynenoate as donor, glycosylation with a series alcohols in presence Ph3PAuOTf and Ph3PO toluene at low temperatures afforded desired glycosides good to excellent β-selectivities. Furthermore, was effectively applied β-(2→4)- β-(2→8)-linked Kdo-Kdo disaccharides further biological studies.

Language: Английский