Horner-Wadsworth-Emmons Reaction of Unprotected Sugars in Water or in the Absence of Any Solvent: One-Step Access to C-Glycoside Amphiphiles

摘要

The synthesis of C-glycosides in water or in the absence of any solvent from free sugars and beta-keto phosphonates is reported. The methodology permits a one-step access to C-glycoside amphiphiles in moderate-to-good yields. The selectivity (alpha/beta and furanoside/pyranoside) is discussed and a process that leads to pure beta-C-pyranosides is also described.