Synthèse par aldolisation dirigèe des 2-dèsoxy-2-C-mèthylene-D-erythro- ET -D-thréo-pentoses
1980; Elsevier BV; Volume: 83; Issue: 1 Linguagem: Inglês
10.1016/s0008-6215(00)85363-x
ISSN1873-426X
AutoresJean‐Claude Depezay, Yves Le Merrer,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoBranched-chain sugars with a CH2-2 group were obtained by aldol condensation at 70° between 1.1-diethoxy-2-lithio-2-propene and 2,3-O-isopropylidene-D- glyceraldehyde. Depending on the experimental procedure, hydrolysis in acidic medium of the products, precursors of C-2 branched-chain pentoses, led to methyl 2-deoxy-2-C-methylene-β-D-erythro- and -α-D-threo-pentopyranosides, 2,4-disubstituted furans, or unsaturated aldehydes transformed into the corresponding α methylenelactones.
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