1-decyne -Drug Synthesis Database

【结构式】

【分子编号】42585

【品名】1-decyne

【CA登记号】764-93-2

【分子式】C₁₀H₁₈

【分子量】138.25292

【元素组成】C 86.88% H 13.12%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(II)

Coupling of 5-iodo-2'-deoxyuridine (I) with 1-decyne (II) in the presence of cuprous iodide and tetrakis(triphenylphosphine)palladium furnished the 5-decynyl uridine derivative (III). This was then cyclized to the title furopyrimidinone by treatment with cuprous iodide and triethylamine in refluxing methanol.

参考文献中间体

合成目标

【1】 Balzarini, J.; McGuigan, C.; Andrei, G.; Srinivasan, S.; Snoeck, R.; De clercq, E.; Bicyclic nucleoside inhibitors of varicella-Zoster virus (VZV): The effect of terminal unsaturation in the side chain. Bioorg Med Chem Lett 2001, 11, 3, 391.
【2】 Brancale, A.; Snoeck, R.; Yarnold, C.J.; Barucki, H.; Velázquez, S.; Jones, G.; Andrei, G.; McGuigan, C.; De Clercq, E.; Balzarini, J.; Potent and selective inhibition of varicella-zoster virus (VZV) by nucleoside analogues with an unusual bicyclic base. J Med Chem 1999, 42, 22, 4479.
【3】 Jones, G.; Balzarini, J.; McGuigan, C.; Yarnold, C.; De Clercq, E. (University College, Cardiff); Anti-viral pyrimidine nucleoside analogues. EP 0980377; WO 9849177 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	31154	1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-iodo-2,4(1H,3H)-pyrimidinedione	54-42-2	C₉H₁₁IN₂O₅	详情	详情
(II)	42585	1-decyne	764-93-2	C₁₀H₁₈	详情	详情
(III)	42586	5-(1-decynyl)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione		C₁₉H₂₈N₂O₅	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VII)

In another synthetic route, the starting 3',5'-di-O-acetyl-5-iodo-2'-deoxyuridine (IV) was converted to the corresponding 4-thio derivative (V) upon treatment with P2S5. This was S-methylated with iodomethane and triethylamine to give the 4-methylthio pyrimidinone (VI). Palladium-catalyzed coupling of this 5-iodopyrimidine (VI) with 1-decyne (VII) furnished the 5-decynyl nucleoside (VIII). Removal of the methylthio group with NaSH in DMF gave directly the cyclized thienopyrimidine (IX). The remaining acetate esters were finally hydrolyzed by treatment with a methanolic solution of ammonium hydroxide.

参考文献中间体

合成目标

【1】 Brancale, A.; et al.; Bicyclic anti-VZV nucleosides: Thieno analogues retain full antiviral activity. Bioorg Med Chem Lett 2001, 11, 18, 2507.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	52282	{3-(acetyloxy)-5-[5-iodo-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl}methyl acetate		C₁₃H₁₅IN₂O₇	详情	详情
(V)	52283	{3-(acetyloxy)-5-[5-iodo-2-oxo-4-thioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-2-furanyl}methyl acetate		C₁₃H₁₅IN₂O₆S	详情	详情
(VI)	52284	{3-(acetyloxy)-5-[5-iodo-4-(methylsulfanyl)-2-oxo-1(2H)-pyrimidinyl]tetrahydro-2-furanyl}methyl acetate		C₁₄H₁₇IN₂O₆S	详情	详情
(VII)	42585	1-decyne	764-93-2	C₁₀H₁₈	详情	详情
(VIII)	52285	{3-(acetyloxy)-5-[5-(1-decynyl)-4-(methylsulfanyl)-2-oxo-1(2H)-pyrimidinyl]tetrahydro-2-furanyl}methyl acetate		C₂₄H₃₄N₂O₆S	详情	详情
(IX)	52286	2-[(acetyloxy)methyl]-5-[6-octyl-2-oxothieno[2,3-d]pyrimidin-3(2H)-yl]tetrahydro-3-furanyl acetate		C₂₃H₃₂N₂O₆S	详情	详情

Extended Information