124044-01-5Relevant academic research and scientific papers
Synthesis of Cyclopropanated and Branched-Chain Pyranosides via Carbohydrate Triflates
Fatima, Ayjaz,Zaman, Fakhar,Shekhani, Mohammed Saleh,Malik, Abdul,Voelter, Wolfgang
, p. 389 - 392 (2007/10/02)
Approaches to the cyclopropanated pyranosides benzyl 3,4-("exo"-cyano)methano-3,4-dideoxy-β-L-arabinopyranoside (5) and benzyl 3,4-("exo"-cyano)methano-3,4-dideoxy-α-D-arabinopyranoside (6) and the branched-chain epoxy sugars benzyl-2,3-anhydro-4-(tert-butoxycarbonyl)methyl-4-deoxy-β-L-lyxopyranoside (7) and benzyl 2,3-anhydro-4-(tert-butoxycarbonyl)-methyl-4-deoxy-α-D-lyxopyranoside (8) by displacement of the triflate group with carbanions are described.Preparation of biologically important sugars bearing peptides has been demonstrated by reduction of 5 and 6 to benzyl 3,3-("exo"-aminomethyl)methano-3,4-dideoxy-β-L-arabinopyranoside (9) and benzyl 3,4-("exo"-aminomethyl)methano-3,4-dideoxy-α-D-arabinopyranoside (10) and the coupling of the resulting amines with protected L-alanine.
