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Article Dans Une Revue Carbohydrate Research Année : 2022

Metal-free hydroxy and aminocyanation of furanos-3-uloses

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Résumé

TSAO-T and ATSAO-T analogues are molecules of interest that are able to inhibit the reverse transcriptase (RT) of HIV-1 and HCV. We also recently highlighted their antiproliferative properties. In all cases, the spiro cycle was a required group for biological activities, which led chemists to produce many derivatives, especially on this ring. These structures can be accessed through the formation of glycoaminonitriles and glycocyanhydrins using methodologies not always adapted to the synthesis of large quantities. Moreover, these latter are poorly versatile (substrate-dependent), need expensive cyanogenic agents and implies the use of a metal in non-catalytic amounts. For this reason, we report here a new metal-free methodology for the synthesis of glycoaminonitriles and glycocyanhydrins using molecular iodine (I-2).

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Chimie
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Dates et versions

hal-03745876 , version 1 (04-08-2022)

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Tchambaga Etienne Camara, Dindet Steve-Evanes Koffi Teki, Vincent Chagnault. Metal-free hydroxy and aminocyanation of furanos-3-uloses. Carbohydrate Research, 2022, 511, ⟨10.1016/j.carres.2021.108486⟩. ⟨hal-03745876⟩
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