Chemistry of O-Silylated Ketene Acetals: Stereocontrolled Synthesis of 2-Deoxy- and 2-Deoxy-2-C-alkyl-erythro-pentoses
Diastereoselective aldol reactions of 2,3-O-isopropylidene-D-(and L-)-glyceraldehydes (D- and L-2) with ketene silyl acetal 1a occurred in acetonitrile under mild conditions to give the corresponding anti-β-siloxy esters (D- and L-3a) as major products, which were converted to 2-deoxy-D-(and L-) riboses through a few additional steps.The aldol reactions of D-2 with α-monoalkyl-substituted ketene silyl acetals 1c-f proceeded similarly to give all anti-α-alkyl-β-siloxy esters (11a-14a) as major products, which were converted into 2-deoxy-2-C-alkyl-erythro-pentoses (17a,b).
THE CHEMISTRY OF O-SILYLATED KETENE ACETALS; DIASTEREOSELECTIVE ALDOL REACTION OF 2,3-O-ISOPROPYLIDENE-D (AND L)-GLYCERALDEHYDES LEADING TO 2-DEOXY-D (AND L)-RIBOSES
Diastereoselective carbon-carbon bond forming reaction of 2,3-O-isopropylidene-D (and L)-glyceraldehydes (D and L-2) with ketene silyl acetals (1a,b) occured in acetonitrile under mild conditions to give the corresponding anti-β-siloxyesters (D and L-3a) as major products, which could be converted through a few additional steps to 2-deoxy-D (and L)-riboses.
Kita, Yasuyuki,Yasuda, Hitoshi,Tamura, Osamu,Itoh, Fumio,Ke, Ya Yuan,Tamura, Yasumitsu
p. 5777 - 5780
(2007/10/02)
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