1334652-47-9Relevant articles and documents
Stereodivergent synthesis of diastereoisomeric carba analogs of glycal-derived vinyl epoxides: A new access to carbasugars
Frau, Ileana,Bussolo, Valeria Di,Favero, Lucilla,Pineschi, Mauro,Crotti, Paolo
, p. 820 - 826 (2012/01/13)
A convenient method for the stereoselective synthesis of diasteroisomeric vinyl epoxides (-)-2α and (-)-2β, the carba analogs of D-galactal and D-allal-derived vinyl epoxides 1αand 1β, has been elaborated starting from tri-O-acetyl-D-glucal. The key step of this synthesis is an application of the known Claisen thermal rearrangement of a glucal derivative, the vinyl allyl ether (+)-3b, which allows to switch the glycal structure into the corresponding carba analog scaffold. Epoxides (-)-2α and (-)-2β derive from the same synthetic intermediate, the trans diol (+)-5. Chirality, 2011. 2011 Wiley-Liss, Inc. Copyright