MMdUrd, -Drug Synthesis Database

【结构式】

【药物名称】MMdUrd

【化学名称】2'-Deoxy-5-(methoxymethyl)uridine

【CA登记号】5116-22-3

【分子式】C₁₁H₁₆N₂O₆

【分子量】272.25997

【开发单位】

【药理作用】ANTIINFECTIVE THERAPY, Antiviral Drugs

合成路线1 合成路线2

合成路线1

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.

参考文献中间体

【1】 Gupta, V.S.; Bubbar, G.L.; Synthesis of 5-substituted ether derivatives of 5-hydroxymethyl deoxyuridine and their 'alpha-anomers'. Can J Chem 1970, 48, 20, 3147.
【2】 Gupta, V.S.; Methoxymethyl-2'-deoxyuridine. Drugs Fut 1981, 6, 1, 32.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IVa)	37191	(2R,3S,5R)-5-[5-(methoxymethyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-2-[[(4-methylbenzoyl)oxy]methyl]tetrahydro-3-furanyl 4-methylbenzoate		C₂₇H₂₈N₂O₈	详情	详情
(IVb)	37192	(2R,3S,5S)-5-[2,4-dioxo-5-[[(trimethylsilyl)oxy]methyl]-3,4-dihydro-1(2H)-pyrimidinyl]-2-(hydroxymethyl)tetrahydro-3-furanyl 4-methylbenzoate		C₂₁H₂₈N₂O₇Si	详情	详情
(I)	37189	5-(methoxymethyl)-2,4(1H,3H)-pyrimidinedione		C₆H₈N₂O₃	详情	详情
(II)	37190	5-(methoxymethyl)-2,4-bis[(trimethylsilyl)oxy]pyrimidine; [2,4-bis[(trimethylsilyl)oxy]-5-pyrimidinyl]methyl methyl ether		C₁₂H₂₄N₂O₃Si₂	详情	详情
(III)	37194	(2R,3S)-5-Chloro-2-[[(4-methylbenzoyl)oxy]methyl]tetrahydro-3-furanyl 4-methylbenzoate	4330-21-6	C₂₁H₂₁ClO₅	详情	详情

合成路线2

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.

参考文献中间体

【1】 Gupta, V.S.; Bubbar, G.L.; Synthesis of 5-substituted ether derivatives of 5-hydroxymethyl deoxyuridine and their 'alpha-anomers'. Can J Chem 1970, 48, 20, 3147.
【2】 Gupta, V.S.; Methoxymethyl-2'-deoxyuridine. Drugs Fut 1981, 6, 1, 32.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(V)	11875	1-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione; 2'-Deoxyuridine	951-78-0	C₉H₁₂N₂O₅	详情	详情
(VI)	37193	1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-(hydroxymethyl)-2,4(1H,3H)-pyrimidinedione		C₁₀H₁₄N₂O₆	详情	详情

Extended Information