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- W2085497614 abstract "(2 S )-(2,4,5/3)-2,3,4-Tribenzyloxy-5-(tetrahydropyran-2-yloxy)cyclohexanone ( 9 ), when treated with vinylmagnesium bromide and trimethylsilylmethylmagnesium chloride, gave (1 S )-(1O,2,4,5/1C,3)-2,3,4-tribenzyloxy-5-(tetrahydropyran-2-yloxy)-1-vinylcyclohexanol ( 10 ) and (1 R )-(1O,2,4,5/1C,3)-2,3,4-tribenzyloxy-1-(trimethylsilylmethyl)cyclohexane-1,5-diol ( 16 ), respectively, with the S configuration at C-1 exclusively. Following oxidative cleavage of the double bond, 10 was converted into (1 S )-(1O,2,4,5/1C,3)-1,2,3,4,5-pentabenzyloxy-1-(benzyloxymethyl)cyclohexane ( 14 ), the C-5 epimer 19 of which was obtained from the trimethylsilylmethyl-substituted adduct following hydroxylation of the double bond of the derived (2 R )-(2,4,5/3)-2,3,4-tribenzyloxy-5-hydroxy-1-methylenecyclohexane ( 17 ). (2 S )-(2,4,5/3)-2,3,4-Tribenzyloxy-5-hydroxycyclohexanone ( 7 ) was converted into its enantiomer 26 and into (1 S )-(1O,2,4,5O/1C,5C)-2,3,4-tribenzyloxy-5-(trimethylsilyl)methyl-1-vinylcyclohexane-1,5-diol ( 28 )." @default.
- W2085497614 created "2016-06-24" @default.
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- W2085497614 date "1990-09-01" @default.
- W2085497614 modified "2023-10-14" @default.
- W2085497614 title "Hexa-O-benzyl-5-hydroxy-pseudo-α-d-glucopyranose and its C-5 epimer" @default.
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- W2085497614 doi "https://doi.org/10.1016/0008-6215(90)80147-u" @default.
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