Abstract

A series of 1,5-anhydro-d-glycero-d-gluco-heptitol derivatives have been prepared from 3-O-benzyl-1,2-O-isopropylidene-d-glycero-d-gluco-heptofuranose via conversion into anomeric bromide and thiophenyl derivatives, followed by glycal formation and reductive desulfurization, respectively. Global deprotection of the protected intermediates afforded the 1,5-anhydro derivatives of the d-glycero-d-gluco- and 1,2-dideoxy-d-altro- configuration as well as the 1,5-anhydro-2-deoxy-d-altro-hept-1-enitol. In addition, the 7-O-phosphorylated d-glycero-d-gluco-heptose and its 1,5-anhydro analogue were prepared in good yields utilizing phosphoramidite chemistry. A novel heptitol analogue based on a 1-deoxynojirimycin scaffold was also elaborated via a Wittig­-type chain elongation followed by dihydroxylation, separation of the resulting epimers, and global deprotection. The target compounds, however, were not active as inhibitors of the bacterial sedoheptulose-7-phosphate isomerase GmhA.

A series of 1,5-anhydro-d-glycero-d-gluco-heptitol derivatives have been prepared from 3-O-benzyl-1,2-O-isopropylidene-d-glycero-d-gluco-heptofuranose via conversion into anomeric bromide and thiophenyl derivatives, followed by glycal formation and reductive desulfurization, respectively. Global deprotection of the protected intermediates afforded the 1,5-anhydro derivatives of the d-glycero-d-gluco- and 1,2-dideoxy-d-altro- configuration as well as the 1,5-anhydro-2-deoxy-d-altro-hept-1-enitol. In addition, the 7-O-phosphorylated d-glycero-d-gluco-heptose and its 1,5-anhydro analogue were prepared in good yields utilizing phosphoramidite chemistry. A novel heptitol analogue based on a 1-deoxynojirimycin scaffold was also elaborated via a Wittig­-type chain elongation followed by dihydroxylation, separation of the resulting epimers, and global deprotection. The target compounds, however, were not active as inhibitors of the bacterial sedoheptulose-7-phosphate isomerase GmhA.

中文翻译：

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1,5-脱水-d-甘油-葡萄糖-庚糖醇衍生物的合成作为细菌庚糖生物合成途径的潜在抑制剂

摘要

一系列1,5-脱水-的d -甘油基- d -葡糖-heptitol衍生物已经由3- ø -苄基-1,2- ö异亚丙基d -甘油基- d -葡糖-heptofuranose经由转化为异头溴化物和硫代苯基衍生物，然后分别形成糖基和还原性脱硫。得到的1,5-脱水衍生物被保护的中间体的脱保护全球d -甘油基- d -葡糖-和1,2-二脱氧d -雅卓-配置以及所述1,5-脱水-2-脱氧d -雅卓-庚-1- enitol。此外，7- ö磷酸化的d -甘油基- d -葡糖-heptose及其1,5-脱水类似物是在利用亚磷酰胺化学良好的产率制备。还通过Wittig型链延长，随后的二羟基化作用，所得差向异构体的分离和整体脱保护作用，对基于1-脱氧野oji霉素支架的新型庚醇类似物进行了精心设计。然而，目标化合物没有作为细菌七磷酸七庚糖异构酶GmhA的抑制剂的活性。

一系列1,5-脱水-的d -甘油基- d -葡糖-heptitol衍生物已经由3- ø -苄基-1,2- ö异亚丙基d -甘油基- d -葡糖-heptofuranose经由转化为异头溴化物和硫代苯基衍生物，然后分别形成糖基和还原性脱硫。得到的1,5-脱水衍生物被保护的中间体的脱保护全球d -甘油基- d -葡糖-和1,2-二脱氧d -雅卓-配置以及所述1,5-脱水-2-脱氧d -雅卓-庚-1- enitol。此外，7- ö磷酸化的d -甘油基- d -葡糖-heptose及其1,5-脱水类似物是在利用亚磷酰胺化学良好的产率制备。还通过Wittig型链延长，随后的二羟基化作用，所得差向异构体的分离和整体脱保护作用，对基于1-脱氧野oji霉素支架的新型庚醇类似物进行了精心设计。然而，目标化合物没有作为细菌七磷酸七庚糖异构酶GmhA的抑制剂的活性。