合成路线:3) The reductocondensation of D-glucose (VIII) and butylamine by means of H2 over Pd/C in ethanol gives N-butylglucamine (IX),which is submitted to a biochemical oxidation by means of Gluconobacter oxidans in water to yield 6-(butylamino)-6-deoxy-a-L-sorbofuranose (X).Finally,this compound is submitted to a reductive cyclization with H2 over Pd/C in ethanol/water.4) The selective hydrolysis of 1,2:4,6-di-O-isopropylidene-a-L-sorbofuranose (XI) (together with some of its 1,3:4,6-isomer) by means of H2SO4 in methanol gives 1,2-O-isopropylidene-a-L-sorbofuranose (XII),which is treated with tosyl chloride,triethylamine and pyridine to yield the monotosylated sugar (XIII).Reaction of the protected sugar (XIII) with butylamine in hot pyridine/triethylamine affords 6-(butylamino)-6-deoxy-1,2-O-isopropylidene-a-L-sorbofuranose (XIV),which is finally submitted to a reductive cyclization by means of H2 over Pd/C in water.5) Directly by reductocondensation of 1-deoxynojiri-mycin (XV) with butyraldehyde (XVI) by means of H2 over Pd/C in methanol or with NaBH3CN in methanol/ HCl.
参考文献标题:Use of 1-deoxynojirimycin and its derivs.for treating mammals infected with respiratory syncytial virus
文献作者:Bryant,M.L.; Koszyk,F.J.; Mueller,R.A.; Partis,R.A.(Pharmacia Corp.)
参考来源:WO 9522975
合成路线:1) The reductive ring opening of 2,3,4,6-tetra-O-benzyl-a-D-glucopyranose (I) with LiAlH4 in THF gives the diol (II),which is oxidized by means of DMSO,trifluoroacetic anhydride and triethylamine in dichloromethane to yield the unstable ketoaldehyde (III),which,without isolation,is submitted to a reductocyclization with butyl-amine and NaBH3CN in methanol to afford the protected iminosugar (IV).Finally,this compound is debenzylated by means of Li and NH3 in THF.2) The oxidation of 1,2-O-isopropylidene-5-oxo-a-D-glucofuranose (V) by means of Bu2SnO and Br2 in refluxing methanol provides the 5-oxoglucofuranose derivative (VI),which is hydrolyzed with Dowex 50W-X8 in water to yield 5-oxo-D-glucose (VII).Finally,this compound is submitted to a reductocyclization with butyl-amine and NaBH3CN in methanol.
参考文献标题:Process for producing polyhydroxylated piperidines and pyrrolidines and cpds.thereof
文献作者:Reitz,A.; Baxter,E.(Ortho-McNeil Pharmaceutical,Inc.)
参考来源:WO 9205152
合成路线:3) The reductocondensation of D-glucose (VIII) and butylamine by means of H2 over Pd/C in ethanol gives N-butylglucamine (IX),which is submitted to a biochemical oxidation by means of Gluconobacter oxidans in water to yield 6-(butylamino)-6-deoxy-a-L-sorbofuranose (X).Finally,this compound is submitted to a reductive cyclization with H2 over Pd/C in ethanol/water.4) The selective hydrolysis of 1,2:4,6-di-O-isopropylidene-a-L-sorbofuranose (XI) (together with some of its 1,3:4,6-isomer) by means of H2SO4 in methanol gives 1,2-O-isopropylidene-a-L-sorbofuranose (XII),which is treated with tosyl chloride,triethylamine and pyridine to yield the monotosylated sugar (XIII).Reaction of the protected sugar (XIII) with butylamine in hot pyridine/triethylamine affords 6-(butylamino)-6-deoxy-1,2-O-isopropylidene-a-L-sorbofuranose (XIV),which is finally submitted to a reductive cyclization by means of H2 over Pd/C in water.5) Directly by reductocondensation of 1-deoxynojiri-mycin (XV) with butyraldehyde (XVI) by means of H2 over Pd/C in methanol or with NaBH3CN in methanol/ HCl.
参考文献标题:Process for producing N-substd.-1-deoxynojirimycin
文献作者:Wang,P.T.; Grabner,R.W.; Landis,B.H.; Prunier,M.L.; Scaros,M.G.(Pharmacia Corp.)
参考来源:EP 0477160
合成路线:3) The reductocondensation of D-glucose (VIII) and butylamine by means of H2 over Pd/C in ethanol gives N-butylglucamine (IX),which is submitted to a biochemical oxidation by means of Gluconobacter oxidans in water to yield 6-(butylamino)-6-deoxy-a-L-sorbofuranose (X).Finally,this compound is submitted to a reductive cyclization with H2 over Pd/C in ethanol/water.4) The selective hydrolysis of 1,2:4,6-di-O-isopropylidene-a-L-sorbofuranose (XI) (together with some of its 1,3:4,6-isomer) by means of H2SO4 in methanol gives 1,2-O-isopropylidene-a-L-sorbofuranose (XII),which is treated with tosyl chloride,triethylamine and pyridine to yield the monotosylated sugar (XIII).Reaction of the protected sugar (XIII) with butylamine in hot pyridine/triethylamine affords 6-(butylamino)-6-deoxy-1,2-O-isopropylidene-a-L-sorbofuranose (XIV),which is finally submitted to a reductive cyclization by means of H2 over Pd/C in water.5) Directly by reductocondensation of 1-deoxynojiri-mycin (XV) with butyraldehyde (XVI) by means of H2 over Pd/C in methanol or with NaBH3CN in methanol/ HCl.
参考文献标题:Process for preparation of 1,5-(alkylimino)-1,5-dideoxy-D-glucitol and derivs.thereof
文献作者:Weier,R.M.; Behling,J.R.; Farid,P.; Medich,J.R.; Khanna,I.; Prunier,M.; Scaros,M.(Pharmacia Corp.)
参考来源:WO 9117145
合成路线:3) The reductocondensation of D-glucose (VIII) and butylamine by means of H2 over Pd/C in ethanol gives N-butylglucamine (IX),which is submitted to a biochemical oxidation by means of Gluconobacter oxidans in water to yield 6-(butylamino)-6-deoxy-a-L-sorbofuranose (X).Finally,this compound is submitted to a reductive cyclization with H2 over Pd/C in ethanol/water.4) The selective hydrolysis of 1,2:4,6-di-O-isopropylidene-a-L-sorbofuranose (XI) (together with some of its 1,3:4,6-isomer) by means of H2SO4 in methanol gives 1,2-O-isopropylidene-a-L-sorbofuranose (XII),which is treated with tosyl chloride,triethylamine and pyridine to yield the monotosylated sugar (XIII).Reaction of the protected sugar (XIII) with butylamine in hot pyridine/triethylamine affords 6-(butylamino)-6-deoxy-1,2-O-isopropylidene-a-L-sorbofuranose (XIV),which is finally submitted to a reductive cyclization by means of H2 over Pd/C in water.5) Directly by reductocondensation of 1-deoxynojiri-mycin (XV) with butyraldehyde (XVI) by means of H2 over Pd/C in methanol or with NaBH3CN in methanol/ HCl.
参考文献标题:Antiviral cpds.
文献作者:Partis,R.A.; Mueller,R.A.; Koszyk,F.J.(Pharmacia Corp.)
参考来源:US 5310745
合成路线:1) The reductive ring opening of 2,3,4,6-tetra-O-benzyl-a-D-glucopyranose (I) with LiAlH4 in THF gives the diol (II),which is oxidized by means of DMSO,trifluoroacetic anhydride and triethylamine in dichloromethane to yield the unstable ketoaldehyde (III),which,without isolation,is submitted to a reductocyclization with butyl-amine and NaBH3CN in methanol to afford the protected iminosugar (IV).Finally,this compound is debenzylated by means of Li and NH3 in THF.2) The oxidation of 1,2-O-isopropylidene-5-oxo-a-D-glucofuranose (V) by means of Bu2SnO and Br2 in refluxing methanol provides the 5-oxoglucofuranose derivative (VI),which is hydrolyzed with Dowex 50W-X8 in water to yield 5-oxo-D-glucose (VII).Finally,this compound is submitted to a reductocyclization with butyl-amine and NaBH3CN in methanol.
参考文献标题:A novel process for the synthesis of aza-sugars
文献作者:Lopes,C.R.; Lopes,R.S.C.; Matos,C.R.R.
参考来源:BR 9902585
产品链接: CAS No. 72599-27-0››