Voglibose, A-71100, AO-128, Basen, Glustat
伏格列波糖Chemical Name: N-[2-Hydroxy-1-(hydroxymethyl)ethyl]valiolamine; 2(S),3(R),4(S),5(S)-Tetrahydroxy-N-[2-hydroxy-1-(hydroxymethyl)ethyl]-5-(hydroxymethyl)-1(S)-cyclohexylamine; 3,4-Dideoxy-4-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-2-C-(hydroxymethyl)-D-epi-inositol
CAS No. 83480-29-9, 112653-29-9 (undefined isomer)
项目整合开发状态: Launched-1994
项目研究机构: Takeda (Originator)
合成路线:The acylation of valienamine (I) with benzyloxycarbonyl chloride (II) by means of NaHCO3 in ethyl acetate gives the corresponding N-benzyloxycarbonyl derivative (III),which by reaction with Br2 in water is converted to the cyclic carbamate (IV).Elimination of bromine from (IV) with NaBH4 in water affords the new cyclic carbamate (V),which by hydrolysis with Ba(OH)2 in refluxing water is converted to valiolamine (VI).Finally,this compound is reductocondensed with 1,3-dihydroxyacetone (VII) and sodium cyanoborohydride in DMF 2N HCl.
📌 参考资料/链接：
参考文献标题:N-substituted pseudo-aminosugars,their production and use
文献作者:Horii,S.; Kameda,Y.; Fukase,H.(Takeda Chemical Industries,Ltd.)
参考来源:EP 0056194; US 4701559; US 4777294; US 4803303
📄 详细内容
合成路线:The acylation of valienamine (I) with benzyloxycarbonyl chloride (II) by means of NaHCO3 in ethyl acetate gives the corresponding N-benzyloxycarbonyl derivative (III),which by reaction with Br2 in water is converted to the cyclic carbamate (IV).Elimination of bromine from (IV) with NaBH4 in water affords the new cyclic carbamate (V),which by hydrolysis with Ba(OH)2 in refluxing water is converted to valiolamine (VI).Finally,this compound is reductocondensed with 1,3-dihydroxyacetone (VII) and sodium cyanoborohydride in DMF 2N HCl.
参考文献标题:AO-128
文献作者:Prous,J.; Castar,J.
参考来源:Drugs Fut 1986,11(9),729
合成路线:The acylation of valienamine (I) with benzyloxycarbonyl chloride (II) by means of NaHCO3 in ethyl acetate gives the corresponding N-benzyloxycarbonyl derivative (III),which by reaction with Br2 in water is converted to the cyclic carbamate (IV).Elimination of bromine from (IV) with NaBH4 in water affords the new cyclic carbamate (V),which by hydrolysis with Ba(OH)2 in refluxing water is converted to valiolamine (VI).Finally,this compound is reductocondensed with 1,3-dihydroxyacetone (VII) and sodium cyanoborohydride in DMF 2N HCl.
参考文献标题:Synthesis and alpha-D-glucosidase inhibitory activity of N-substituted valiolamine derivatives as potential oral antidiabetic agents
文献作者:Horii,S.; Fukase,H..; Matsuo,T.; Kameda,Y.; Asano,N.; Matsui,K.
参考来源:J Med Chem 1986,29(6),1038
产品链接: CAS No. 83480-29-9›› 产品链接: CAS No.112653-29-9››