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• W2952009025 abstract "The synthesis of 2'-substituted polyhydroxytetrahydropyrimidines as transition-state mimics of enzymatic glycosidic cleavage has been achieved by using guanylation and cyclization methodologies. The D-galacto type N-hydroxy cyclic guanidino-sugar 21 was synthesized in six steps from amine 7 and thiourea 14 in an overall yield of 59%. To further derivatize compound 21 to incorporate the leaving group moiety, we have synthesized 2-methylsulfanyl compounds 26-29 as key intermediates. The 2-methylsulfanyl group in 29 was displaced with amines, assisted by silver tetrafluoroborate as Lewis acid, to give protected cyclic guanidines 30-32 in moderate yields (60-67%). Removal of the protecting groups in 32 gave the D-galacto-type N-hydroxy cyclic guanidino-sugar 34. The key steps in the synthesis of the 6-deoxy-DL-galacto type N-hydroxy cyclic guanidino-sugars 49, 54, and 64-66 involve cyclization of the appropriate acetal intermediates (45, 50, and 58-60) followed by removal of the protecting groups." @default.
• W2952009025 created "2019-06-27" @default.
• W2952009025 creator A5028003705 @default.
• W2952009025 creator A5056753239 @default.
• W2952009025 date "2000-03-28" @default.
• W2952009025 modified "2023-10-16" @default.
• W2952009025 title "Synthesis of 2-Substituted Polyhydroxytetrahydropyrimidines (<i>N</i>-Hydroxy Cyclic Guanidino-Sugars): Transition-State Mimics of Enzymatic Glycosidic Cleavage" @default.
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• W2952009025 doi "https://doi.org/10.1021/jo9915574" @default.
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