Abstract

Convenient and stereoselective methods for the preparation of 2-deoxy-d-glucose and purine 2-deoxy-α-d-glucopyranonucleosides were developed. Halogen-mediated O-glycosidation of d-glucal by bromine in MeOH followed by reductive removal of the halo group and hydrolysis of methoxy group by zinc in saturated aqueous sodium dihydrogen phosphate gave 2-deoxy-d-glucose. Treatment of 3,4,6-tri-O-acetyl-d-glucal with IBr and 2,6-dichloropurine based on haloetherification and subsequent reductive removal of iodine and deprotection allowed the isolation of purin-9-yl 2-deoxy-α-d-glucopyranonucleoside. Preparation of several purin-9-yl 2-deoxy-α-d-glucopyranoside derivatives is also reported. Their configuration was confirmed by single crystal X-ray analysis of the key intermediate 2,6-dichloro-9-(2-iodo-2-deoxy-α-d-glucopyranosyl)purine.

Convenient and stereoselective methods for the preparation of 2-deoxy-d-glucose and purine 2-deoxy-α-d-glucopyranonucleosides were developed. Halogen-mediated O-glycosidation of d-glucal by bromine in MeOH followed by reductive removal of the halo group and hydrolysis of methoxy group by zinc in saturated aqueous sodium dihydrogen phosphate gave 2-deoxy-d-glucose. Treatment of 3,4,6-tri-O-acetyl-d-glucal with IBr and 2,6-dichloropurine based on haloetherification and subsequent reductive removal of iodine and deprotection allowed the isolation of purin-9-yl 2-deoxy-α-d-glucopyranonucleoside. Preparation of several purin-9-yl 2-deoxy-α-d-glucopyranoside derivatives is also reported. Their configuration was confirmed by single crystal X-ray analysis of the key intermediate 2,6-dichloro-9-(2-iodo-2-deoxy-α-d-glucopyranosyl)purine.

中文翻译：

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来自d-Glucal的2-脱氧-d-葡萄糖和2-脱氧-α-d-吡喃葡萄糖核苷的简便方法

摘要

方便和立体选择性的方法用于制备2-脱氧d葡萄糖和嘌呤-2-脱氧-3-α- d -glucopyranonucleosides被开发出来。卤素-介导的O-苷化d通过在MeOH溴-glucal随后还原除去卤素基团和甲氧基的水解通过在锌饱和的水性磷酸二氢钠，得到2-脱氧- d -葡萄糖。3,4,6-三-治疗ö乙酰基d -glucal与IBR和2,6-二氯嘌呤基于haloetherification和随后的还原去除碘和脱保护允许嘌呤-9-基的隔离2-脱氧- α - d -glucopyranonucleoside。几种嘌呤-9-基2-脱氧-α- d的制备还报道了-吡喃葡萄糖苷衍生物。通过关键中间体2，6-二氯-9-（2-碘-2-脱氧-α- d-吡喃葡萄糖基）嘌呤的单晶X射线分析证实了它们的构型。

方便和立体选择性的方法用于制备2-脱氧d葡萄糖和嘌呤-2-脱氧-3-α- d -glucopyranonucleosides被开发出来。卤素-介导的O-苷化d通过在MeOH溴-glucal随后还原除去卤素基团和甲氧基的水解通过在锌饱和的水性磷酸二氢钠，得到2-脱氧- d -葡萄糖。3,4,6-三-治疗ö乙酰基d -glucal与IBR和2,6-二氯嘌呤基于haloetherification和随后的还原去除碘和脱保护允许嘌呤-9-基的隔离2-脱氧- α - d -glucopyranonucleoside。几种嘌呤-9-基2-脱氧-α- d的制备还报道了-吡喃葡萄糖苷衍生物。通过关键中间体2，6-二氯-9-（2-碘-2-脱氧-α- d-吡喃葡萄糖基）嘌呤的单晶X射线分析证实了它们的构型。