MMdUrd-药物合成数据库

【药物名称】MMdUrd

化学结构式(Chemical Structure):

参考文献No.	237196
标题:	Methoxymethyl-2'-deoxyuridine
作者:	Gupta, V.S.
来源:	Drugs Fut 1981,6(1),32

合成路线图解说明: Treatment of 5-methoxymethyluracil (I) with trimethylchlorosilane in the presence of triethylamine gives bis(trimethylsilyl)-5-methoxymethyluracil (II). Condensation of compound (II) with 3,5-di(0-p-toluoyl)-2-deoxy-D-ribofuranosyl chloride (III) yields an anomeric mixture of blocked nucleosides. The beta-anomer (IVa) is the major product and is purified by crystallization. After deblocking with hot sodium methoxide in methanol, 1-(2-deoxy-beta-D-ribofuranosyl)-5-methoxymethyluracil is obtained.

合成路线图解说明: The reaction of 1-(2-deoxy-beta-D-ribofuranosyl)uracil (V) with CH2O and KOH gives 1-(2-deoxy-beta-D-ribofuranosyl)-5-hydroxymethyluracil (VI), which is treated with methanolic-HCl. Chromatography on silica gel yields the target compound.

参考文献No.	800434
标题:	Synthesis of 5-substituted ether derivatives of 5-hydroxymethyl deoxyuridine and their 'alpha-anomers'
作者:	Gupta, V.S.; Bubbar, G.L.
来源:	Can J Chem 1970,48(20),3147

合成路线图解说明: Treatment of 5-methoxymethyluracil (I) with trimethylchlorosilane in the presence of triethylamine gives bis(trimethylsilyl)-5-methoxymethyluracil (II). Condensation of compound (II) with 3,5-di(0-p-toluoyl)-2-deoxy-D-ribofuranosyl chloride (III) yields an anomeric mixture of blocked nucleosides. The beta-anomer (IVa) is the major product and is purified by crystallization. After deblocking with hot sodium methoxide in methanol, 1-(2-deoxy-beta-D-ribofuranosyl)-5-methoxymethyluracil is obtained.

合成路线图解说明: The reaction of 1-(2-deoxy-beta-D-ribofuranosyl)uracil (V) with CH2O and KOH gives 1-(2-deoxy-beta-D-ribofuranosyl)-5-hydroxymethyluracil (VI), which is treated with methanolic-HCl. Chromatography on silica gel yields the target compound.