[EN] C-GLYCOSIDE AMINE DERIVATIVES AND METHODS OF MAKING<br/>[FR] DÉRIVÉS D'AMINE DE C-GLYCOSIDE ET LEURS PROCÉDÉS DE FABRICATION
申请人:US AGRICULTURE
公开号:WO2021141979A1
公开(公告)日:2021-07-15
Disclosed are C-glycoside amine derivatives of the formula: R-CH2-C(CH3)-NH-R2 wherein R is a saccharide (e.g., as described in U.S. Patent 8,314,219) and R2 is an acyl moiety derived from any ketone of the formula R3-C(O)-R3 wherein R3 is C1 to C22 straight or branched chain hydrocarbon which may be saturated or unsaturated. In addition, a method for making the C-glycoside amine derivatives involving (1) reacting a saccharide (e.g., glucose) C-glycoside ketone with a catalyst (e.g., Rh), about 10 to about 25 fold excess NH3, and an organic solvent (e.g., methanol) to form a saccharide C-glycoside amine, and (2) reacting said saccharide C-glycoside amine with a catalyst (e.g., Rh), an organic solvent (e.g., methanol), and an acyl moiety derived from any ketone of the formula R3-C(O)-R3 wherein R3 is C1 to C22 straight or branched chain hydrocarbon which may be saturated or unsaturated to form said C-glycoside amine derivative.
本发明公开了C-糖苷胺衍生物的结构式:R-CH2-C(CH3)-NH-R2,其中R是一种糖苷(例如,如美国专利8,314,219所述),而R2是从任何公式为R3-C(O)-R3的酮中派生的酰基基团,其中R3是C1到C22的直链或支链烃基,可以是饱和的或不饱和的。此外,本发明还公开了一种制备C-糖苷胺衍生物的方法,包括(1)将糖苷(例如葡萄糖)C-糖苷酮与催化剂(例如Rh)、约10到约25倍过量的NH3和有机溶剂(例如甲醇)反应,以形成糖苷C-糖苷胺,以及(2)将所述糖苷C-糖苷胺与催化剂(例如Rh)、有机溶剂(例如甲醇)和从任何公式为R3-C(O)-R3的酮中派生的酰基基团(其中R3是C1到C22的直链或支链烃基,可以是饱和的或不饱和的)反应,以形成所述C-糖苷胺衍生物。