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- W2000644628 endingPage "2016" @default.
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- W2000644628 abstract "Carbocyclic Compounds from Monosaccharides. 1. Transformations in the Glucose Series A method for the preparation of pentasubstituted cyclopentanes from monosaccharides is presented, involving two crucial steps, viz. the reductive fragmentation of 5-bromo-5-deoxyglucosides (such as 10, 17 and 23, see Scheme 3) with Zn or butyl lithium yielding 5,6-dideoxy-hex-5-enoses (such as 11 and 24, see Schemes 3 and 4), and the subsequent cyclization of these hexenoses with N-methyl- or N-(alkoxyalkyl)hydroxylamines (via the corresponding nitrones) to form cyclopentano-isoxazolidines (see Scheme 2). Thus, the glucosides 17 and 23 were converted diastereoselectively and in good yields into the cyclopentano-isoxazolidines 27 and 45 (Schemes 5 and 7), which were characterized by their transformation into various derivatives. 27 and 45 were correlated through the common derivative 62. The configuration of the cyclization products were established by pyrolysis of the N-oxide 65 to the enol ether 67 (Scheme 10)." @default.
- W2000644628 created "2016-06-24" @default.
- W2000644628 creator A5070811586 @default.
- W2000644628 creator A5075695962 @default.
- W2000644628 date "1979-09-19" @default.
- W2000644628 modified "2023-10-02" @default.
- W2000644628 title "Carbocyclische Verbindungen aus Monosacchariden. I. Umsetzungen in der glucosereihe" @default.
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- W2000644628 doi "https://doi.org/10.1002/hlca.19790620629" @default.
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