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- W2093234474 abstract "(2S,3S)-2,3-Isopropylidenedioxybutyraldehyde, produced by ozonolysis of the O-isopropylidenated (2S,3R)-2,3-diol formed from cinnamaldehyde in fermenting baker's yeast, affords, with diallyl-zinc, the C7, carbohydrate-like, noncarbohydrate-derived adduct (2S,3R,4R)-2,3-isopropylidenedioxy-4-hydroxyhept-6-ene (9). This material is a stereochemically defined, functionalised, chiral synthon which is useful in the synthesis of enantiomerically pure products. The synthesis of the N-trifluoroacetyl derivatives of 4-amino-2,4,6-trideoxy-l-lyxo (21), -l-arabino (22), and -l-ribo-hexose (23) from 9 is reported. Key intermediates in the synthesis were the isomeric epoxy alcohols (2S,3S,4S)-3,4-epoxyhept-6-en-2-ol, (2S,3R,4S)-2,3-epoxyhept-6-en-4-ol, and (2S,3R,4R)-2,3-epoxyhept-6-en-4-ol. The nitrogen function is introduced by intramolecular epoxide-opening of the corresponding benzyl urethanes which gave, eventually, (2S,3R,4S)-3-N-trifluoroacetamidohept-6-en-2,4-diol, (2S,3S,4S)-3-N-trifluoroacetamidohept-6-en-2,4-diol, and (2S,3S,4R)-3-N-trifluoroacetamido-6-en-2,4-diol, from which the required C6-N frameworks of 21–23 were obtained by ozonolysis." @default.
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- W2093234474 date "1985-02-01" @default.
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- W2093234474 title "Carbohydrate-like chiral synthons: Synthesis of the N-trifluoroacetyl derivatives of 4-amino-2,4,6-trideoxy-l-lyxo-, -l-arabino, and -l-ribo-hexose from the (2S,3R)-2,3-diol formed from cinnamaldehyde in fermenting baker's yeast" @default.
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- W2093234474 doi "https://doi.org/10.1016/0008-6215(85)85190-9" @default.
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