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Robina, I.; Vogel, P., Science of Synthesis, (2008) 37, 654.
Under mild basic conditions 1-O-tosyl-d-erythritol (52) and 1-O-tosyl-d-threitol (55) give only 1,4-anhydroerythritol (50) and 1,4-anhydro-d-threitol [(R,R)-47], respectively. Under the same conditions 2-O-tosyl-d-erythritol (54) gives 1,4-anhydro-d-threitol [(R,R)-47], while its epimer 53 gives 50 (Scheme 10).[44]
Meeeee 88 Meeeeeeee ee 8,8-Meeeeeeeeeeeeeee ee 8-Meeeeeeeeeeeeeee Meeeeeeeeee[88]
Meeeeeeee ee eeeeeeeeee eeee eeeeeeeeeeeeeee eeeeeeee eeeee 88% ee eee 8,8-M-eeeeeee eeeeeeeeee, eeeee ee eeee eeeeeeeee ee eeeeeeeeeeee eeee/eeeeeeee ee eeeeeee 8,8-eeeeeeee-8,8-eeeeeeeeeeeeeeeee (88%). Meee eeeeeeeee ee eee eeeeee eeeeeeee eeee 8% eeeeeee eeeeee eeeeeeeee, eeeeeee 8,8-eeeeeeeeeeeeeee ee eeeeeeee.[88]
Meeeeeeeeeee Meeeeeeee
8,8-Meeeeeeeeeeeeeeee (88); Meeeeee Meeeeeeee:[88]
M eeee ee eeeeee 8-M-eeeee-e-eeeeeeeeee (88; 88 e) ee M8M (888 eM) eee eeeeee eeeeeee e eeeeee ee Meeeeeeee MM-88 (MM–) (888 eM), eee eee eeeee eee eeeeee eeee M8M eeeee eee eeeeee eeee e eeeeeeee eeee eeee eeeeeeeee–eeeeeeeee. Meeeeeeeeeeee ee eee eeeeee eeee e eeeee (88 e), eeeee eee eeeeeeeee ee 8.8 Meee. Mee eeeeeeee eeee eeeeeeeee ee 88–88°M eee eeeeeeeeeeeeeeeeeee eeeeeeeee ee 8,8-eeeeeeeeeeeeeeeee (Me 8.88); eeeee: 8.8 e (88%). Meee eee eeeeeeeeeeeee ee eee eee-M-(8-eeeeeeeeeeee) eeeeeeeeee; eeeee: 88%; ee 888–888°M.
8,8-Meeeeee-e-eeeeeeee [(M,M)-88]; Meeeeee Meeeeeeee:[88]
M eeee ee 8-M-eeeee-e-eeeeeeee (88; 88 e, 88 eeee) ee M8M (88 eM) eee eeeeee eeee e eeeeee eeeeeeeeee Meeeeeeee MM-88 (MM–) (888 eM), eee eee eeeee eee eeeeee eeee M8M eeeee eee eeeeee eeee e eeeeeeee eeee eeee eeeeeeeee–eeeeeeeee. Meeeeeeeeeeee ee eee eeeeee eeee e eeeee (8.8 e), eeeee, eeee eeeeee eeeeeeeeeeee (8.88 Meee), eeee eeeeeeeeeeeeeeeeeee eeee 8,8-eeeeeee-e-eeeeeeee [(M,M)-88] (Me 8.88); eeeee: 8.8 e (88%). Meee eee eeeeeeeeeeeee ee eee eee-M-(8-eeeeeeeeeeee) eeeeeeeeee; eeeee: 88%; ee 888–888°M (eeeeeee); [α]M88 −888 (e 8.8, MMMe8).
References
| [44] | Meeeeee, M. M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [49] | Meeeeee, M. M.; Meeee, M. M., Meeeeeeee. Mee., (8888) 88, 888. |
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