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Acetals and Ketals of the Tetritols. Pentitols and Hexitols

Elsevier Science & Technology
DOI: 10.1016/s0096-5332(08)60084-3


Publisher Summary The chapter focuses on the acetals and ketals that are formed from tetritols, pentitole, and hexitols, on the one hand, and the simpler carbonyl compounds (e.g., acetone and benzaldehyde), on the other. With the aid of these rules, (1) the first preference is for α βC-ring, (2) the second preference is for a β-ring, (3) the third preference is for an α-, αT-, βT-, or γT-ring, and (4) in methylenation, a βT-ring takes precedence over an αT- or γT-ring and in benzylidenation and ethylidenation, an αT-ring takes precedence over a βT- or γT-ring––the structures of the acetals is predicted that would be expected to result from the benzylidenation, ethylidenation, and methylenation of all the tetritols, pentitols and hexitols. The rules explain the syntheses of 3,5-benzylidene- and 3,5-methylene-glucogulo-heptitol, 1,3:5,7-dibenzylidene- and 1,3:5,7-dimethylene-D-perseitol, and 2,3-dibenzoyl-5,6-benzylidene-l,4-anhydro-D-mannitol.

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