Diphenylphosphinoylethylidene (DPE) acetals: an alternative protective strategy in glycochemistry

✍ Scribed by Leonardo Pellizzaro; Arnaud Tatibouët; Fabrizio Fabris; Patrick Rollin; Ottorino De Lucchi

• Publisher: Elsevier Science
• Year: 2009
• Tongue: French
• Weight: 187 KB
• Volume: 50
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2008.10.111

✦ Synopsis

b s t r a c t Diphenylphoshinoylethyne reacts with diols under basic conditions to produce cycloacetalic phosphine oxides. The reaction appears to be general and particularly effective with carbohydrate derivatives. The 2-(diphenylphoshinoyl)ethylidene (DPE) acetals produced are stable in acidic media while they can be cleaved under reductive and/or basic conditions: base-catalyzed transacetalization is a method of choice for their mild and effective deprotection.