163810-82-0Relevant academic research and scientific papers
An alternative synthesis of (+) - epiallo-muscarine from D-glucose
Popsavin, Velimir,Beric, Ostoja,Popsavin, Mirjana,Csanadi, Janos,Miljkovic, Dusan
, p. 343 - 348 (1995)
Keywords: 2,5-Anhydro sugars; Chiral synthon; (+)-epiallo-Muscarine
Dioxolane acetal ring expansion during a sugar triflate displacement. Synthesis and assignment of diastereoisomer configuration of novel 9-crown-3 ether derivatives
Popsavin, Velimir,Beri?, Ostoja,Popsavin, Mirjana,Csanádi, János,Vuji?, Djura,Hrabal, Richard
, p. 3629 - 3632 (1999)
Treatment of 2,5:3,6-dianhydro-6-thio-4-O-trifluoromethanesulfonyl-L- talose ethylene acetal (5) with lithium benzoate in boiling DMF unexpectedly gave the 9-crown-3 ether derivatives 7 and 8 instead of the substitution product 6. The mechanism of the pro
Stereospecific synthesis of (-)-allo-muscarine from D-glucose: Novel routes to the key chiral synthon
Popsavin, Velimir,Beric, Ostoja,Popsavin, Mirjana,Csanadi, Janos,Lajsic, Stevan,Miljkovic, Dusan
, p. 809 - 815 (2007/10/03)
The key chiral synthon in a novel synthesis of (-)-allo-muscarine from D-glucose has been prepared by three independent routes. The most efficient one includes a four-step conversion via the 4-O-benzoyl derivatives of starting 2,5-anhydro-3,5-di-O-methanesulfonyl-L-idose ethylene acetal (2a) into 2,5-anhydro-3,6-dideoxy-L-lyxo-hexose ethylene acetal (4b). The intermediate 4b was efficiently converted into the chiral synthon 2,5-anhydro-4-O-benzoyl-3,6-dideoxy-L-arabino-hexose (4c) by Mitsunobu reaction.
