D‐Aldoses with up to nine C atoms have been synthesized stepwise by homologation of the glyceraldehyde derivative 1. The two key steps are the anti diastereoselective addition of 2 to an α‐chiral aldehyde and the conversion of the thiole ring in the adduct into the formyl group. The reaction sequence 1+2→3→4 illustrates the principle of the reaction. (Figure Presented.) Copyright © 1986 by VCH Verlagsgesellschaft mbH, Germany
Synthesis of long-chain sugars by iterative diastereselective homologation of 2,3-O-isopropylidene-D-glyceraldehyde with 2-trimethylsilylthiazole
DONDONI, Alessandro;FANTIN, Giancarlo;FOGAGNOLO, Marco;MEDICI, Alessandro
1986
Abstract
D‐Aldoses with up to nine C atoms have been synthesized stepwise by homologation of the glyceraldehyde derivative 1. The two key steps are the anti diastereoselective addition of 2 to an α‐chiral aldehyde and the conversion of the thiole ring in the adduct into the formyl group. The reaction sequence 1+2→3→4 illustrates the principle of the reaction. (Figure Presented.) Copyright © 1986 by VCH Verlagsgesellschaft mbH, GermanyFile in questo prodotto:
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