Glycosyl chlorides, useful as glycosyl donors in glycoside synthesis and precursors in organic synthesis, can be easily prepared under solvent-free conditions by exposing a sugar hemiacetal to an equimolar mixture of PPh3 and hexachloroacetone at 70 C. The reaction affords products in high yields and short times, and is tolerant of a wide range of commonly adopted protecting groups.
Solvent-free synthesis of glycosyl chlorides based on the triphenyl phosphine/hexachloroacetone system / Traboni, Serena; Liccardo, Federica; Bedini, Emiliano; Giordano, Maddalena; Iadonisi, Alfonso. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 58:(2017), pp. 1762-1764. [10.1016/j.tetlet.2017.03.068]
Solvent-free synthesis of glycosyl chlorides based on the triphenyl phosphine/hexachloroacetone system
TRABONI, SERENA;BEDINI, EMILIANO;GIORDANO, MADDALENA;IADONISI, ALFONSO
2017
Abstract
Glycosyl chlorides, useful as glycosyl donors in glycoside synthesis and precursors in organic synthesis, can be easily prepared under solvent-free conditions by exposing a sugar hemiacetal to an equimolar mixture of PPh3 and hexachloroacetone at 70 C. The reaction affords products in high yields and short times, and is tolerant of a wide range of commonly adopted protecting groups.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
