1,2:3,4-di-O-isopropylidene-α-D-galacto-hexodialdo-1,5-pyranose and its 6-aldehydrol
1968; Elsevier BV; Volume: 7; Issue: 1 Linguagem: Inglês
10.1016/s0008-6215(00)81433-0
ISSN1873-426X
AutoresDerek Horton, Masahiro Nakadate, J. M. J. TRONCHET,
Tópico(s)Synthesis of Organic Compounds
ResumoOxidation of 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (1) with methyl sulfoxide-N,N′-dicyclohexylcarbodiimide-pyridinium phosphate (Pfitzner-Moffatt reagent) furnishes a preparative route to the title aldehyde 2. In aqueous solution, 2 exists entirely in the form of its 6-aldehydrol (8). In common with a number of other aldehydo sugar derivatives, compound 2 exhibits zero spin-coupling between the aldehyde proton and the proton vicinal to it. The aldehyde 2 was characterized as the crystalline 6-oxime (3) and 6-(p-nitrophenyl)hydrazone (7). Compounds 2, 3, and 7 are important as potential intermediates in chain-extension reactions leading to 6-amino-6,8-dideoxy-octoses related to lincomycin.
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