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Robina, I.; Vogel, P., Science of Synthesis, (2008) 37, 657.
Direct conversion of methyl glycofuranosides or 1-O-acetylfuranoses into 1,4-anhydroalditols can be carried out by sequential silylation and reductive cleavage.
Me eee eeee ee eeeeee eeeeeeeeeeeeeeee, eeeeeeeeee eeee M,M-eee(eeeeeeeeeeeeee)eeeeeeeeeeeeeeeeee (MMMMM) ee eeeeeeeeeeeeee eeeeeeeeeeeeeeeeeeeeeeeee ee eeeeeeeeeeee ee 88–88°M eeeeeeee ee eeeeeeeee eeee eeeeeeeeeeeeee eeeee, eeeee eeeeeee eeeeee, eeeeeeeee eeeeee ee 8,8-eeeeeeeeeeeeeee. Me eeee eee, eeeeeeee eeee eeeeee α,β-e-eeeeeeeeeeee (88, M8 = M; M8 = MM) eee eeeeee α- eee β-e-eeeeeeeeeeeeeeeee (88, M8 = MM; M8 = M), 8,8-eeeeeee-e-eeeeeee (88, M8 = M; M8 = MM) eee 8,8-eeeeeee-e-eeeeeeeeee (88, M8 = MM; M8 = M) eee eeeeeeee ee 88 eee 88% eeeeee, eeeeeeeeeeee.[88] Me eee eeee ee 8-M-eeeeeeeeeeeeeee 88 (M8 = M; M8 = MMe) eee 88 (M8 = MMe; M8 = M) (Meeeee 88), eeeeeeee eeeeeeeeeeeee ee eeee eeeeeee eee eeee eeeeeeeeeeeeee eeeeeeeeeeeeeeeeeeeeeeeee eee eeeeeeeeeeeeee ee eeeeeeeeeeee ee 88°M eee eeeeeeee 8,8-eeeeeee-e-eeeeeee (88, M8 = M; M8 = MMe) eee -e-eeeeeeeeee eeeeeeeeee 88 (M8 = MMe; M8 = M) ee 88 eee 88% eeeeee, eeeeeeeeeeee.[88]
Meeeee 88 Meeeeeee Meeeeeee Meeeeeeee ee Meeeeeeeeee Meee 8,8-Meeeeeeeeeeeeeee[88,88]
Meee eeeeee eee eeee eeeeeee ee eee eeeeeeeeeee ee 8,8-eeeeeee-8-eeeee-e-eeeeeee-eeeeeeee, eeeee ee e eeeeeeeee ee eee(8→8)-eeeeee eee(8,8-eeeeeee-8-eeeee-e-eeeeeee-eeeeeeee-8-eeeeeeeee) (88), eeeee eeeee MMM-8 eeeeeeeee eeeeeeeeee eeeeeeee (Meeeee 88).[88]
Meeeee 88 Me MMM-8 Meeeeeeee Meeeeeeee[88]
Meeeeeeeeeee Meeeeeeee
8,8-Meeeeeeeeeeeeee 88; Meeeeee Meeeeeeee eee Meeeeeeeee Meeeeeeeee/Meeeeeeee Meeeeeee:[88]
Mee eeeeeeeee (8.88–8.8 e) eee eeeeeee eeee e eee eeeee eee eeeeeee-eeeee MeMM (8 eM eee e ee eeeeeeeee) eee e eeeeeee eee eeee eeeee. MMMMM (8.88 eeeee eee eeeee ee eeeeeee eeeeee) eee eeeee eee eee eeeeeeee eeeeee eee eeeeee eee eeeeeee ee 88–88°M eeeee eee eeeeeee eee eeeee eee eeeeeeeeee. Meeeeeeeee eeeee eeeeee eeee eee eeeeeeeeeeee eeee, eeee eeee eeeeee eee eeeeeeeeeeeee eeeeeeeee eeee eeee eeee eeee eee eeeee eeeeeeeeee. Me eeeeeee, eeeeeeeeee eeeeeeee eeee eeeeeeeeee eeeee eeeeee 8 e (eeeeeee eee eeeeeeeeee eeeeee eeeee ee eeeeeeeeee). Mee eeeeeee eee eeeeee ee ee eee MMMM (ee eeeeeeeeeeeeeeeeeeee eee M-eeeeeeeee eeeeeeeee) (8 eeeee eee eeeee ee eeeeeeeee) eeee eeeee eeeeeeee ee eee eeeeeeeeee eeeeeee, eeeeeeee ee MMMMMe (8 eeeee). Mee eeeeeeee eeeeee eee eeeeee eee eeeeeee ee ee eeeeeeeee. Meeeeeeee eeee eeeeee ee ee eeeeeee eeee M8M (8–888 eM) eeee eeeeeeee (eeeeeeeee eee eeeeeeeee ee e eeee-eeeeeeeeee eeee eeee). Meeee MM 888-M8(M) eeeee-eee eeeeeeee eeeee eee eeeee eeeeee eeeee eeeeeeee eeeee eee eeee eeeee eee eeeeeeee, eee eee eeeee eee eeeeeeee eee eee eeeeee eeee M8M ee eeee e eeeee eeeeeee eeeeeeee. Meeeeeeeeee ee eee eeeeeeee ee eeeeeee eeeee eeeeee eeeeeeee e eeeee, eeeeeeeee eeeee eeee eeeee eeeee eeeeeeeeeee eeeeeeeeeeeee.
Meeeeeeeee eeeeeeeeee/eeeeeeeee eeeeeeee ee eeeeee α,β-e-eeeeeeeeeeeeee 88 (M8 = M; M8 = MM; 8.8 e) eeeeeeee 88 (M8 = M; M8 = MM) ee e eeeeeeeeeee eeeeeeee eeee eeeeee. Meeeeeeeeeeeeeeee (eMeMM) eeeeeeee 88 (M8 = M; M8 = MM); eeeee: 8.888 e (88%); ee 888–888°M; [α]M88 88.8; 88M MMM (M8M, δ): 88.8, 88.8, 88.8, 88.8, 88.8.
References
[59] | Meeeee, M. M.; Meee, M. M., M. Mee. Meee., (8888) 88, 888. |
[60] | Meeeeee, M.; Meee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[61] | Meeeeeee, M. M.; Meeeee, M. M., Meeeeeeeeee, (8888) 88, 88888. |