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• W2066626098 abstract "The synthesis of 2-deoxy-α-DAH ( 2 ) is described based on the use of diazo chemistry as previously reported by us during the synthesis of the corresponding 2-deoxy-KDO. Initially, the d -arabino-aldehydo sugar derivative 3 was reacted with ethyl diazoacetate, using diethyl zinc as promoter. The corresponding β-hydroxy-α-diazo ester 4 , obtained in very good yield, was transformed into the corresponding 2-diazo-3-deoxy-heptulosonate derivative 10 , which was subjected to the action of rhodium(II). However, the major compound obtained in this reaction was the C-glycofuranoside 12 by the interaction of the benzyl protecting group employed at the OH of C-4 with the carbenoid generated at C-2. To avoid this undesired insertion reaction, aldehyde 13 was selected as a suitable starting material and, following the same chemistry than for 3 , diazo 19 was efficiently synthesized. Finally, the intramolecular OH insertion mediated by rhodium(II) of 19 provided the targeted 2-deoxy-DAH derivative 21 in a reasonable good yield, which was finally transformed into the potassium salt of 2-deoxy-α-DAH 2 . Graphic" @default.
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• W2066626098 date "2001-12-01" @default.
• W2066626098 modified "2023-10-01" @default.
• W2066626098 title "Synthesis of 2-deoxy-α-DAH based on diazo chemistry by insertion reactions of 2-diazo-3-deoxy- d - arabino -heptulosonate derivatives mediated by rhodium(II)" @default.
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• W2066626098 doi "https://doi.org/10.1016/s0040-4020(01)01074-2" @default.
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