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【结 构 式】 
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【分子编号】39190 【品名】(2R,3R,4R,5R)-4-(acetoxy)-2-[(acetoxy)methyl]-5-isocyanatotetrahydro-3-furanyl acetate 【CA登记号】 |
【 分 子 式 】C12H15NO8 【 分 子 量 】301.25304 【元素组成】C 47.84% H 5.02% N 4.65% O 42.49% |
合成路线1
该中间体在本合成路线中的序号：(III)The reaction of 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose (I) with dry HCl in ether-acetic anhydride gives 1-chloro-2,3,5-tri-O-acetyl-beta-D-ribofuranose (II), which by reaction with silver isocyanate in dry xylene is converted into 2,3,5-tri-O-acetyl-beta-D-ribofuranosylisocyanate (III). The reaction of (III) with 2-methylisourea (IV) in dry CHCl3 affords 1-(2,3,5-tri-O-acetyl-3-D-ribofuranosyl)-4-methylisobiuret (V), which is cyclized by reaction with ethyl orthoformate at 135 C yielding 1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-4-methoxy-2-oxo-1,2-dihydro-1,3,5-triazine (VI). Finally, this compound is treated with ammonia in dry methanol.
| 【1】 Sorm, F.; Piskala, A.; Nucleic acid components and their analogues. LI. Synthesis of 1-glycosyl derivatives of 5-azauracil and 5-azacytosine. Coll Czech Chem Commun 1964, 29, 2060-76. |
| 【2】 Von Hoff, D.D.; Azacitidine. Drugs Fut 1980, 5, 8, 392. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 12304 | N-[(3R)-9-(2-cyanoethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-4-fluorobenzenesulfonamide | C21H20FN3O2S | 详情 | 详情 | |
| (I) | 33835 | (2R,3R,4R,5S)-4,5-bis(acetoxy)-2-[(acetoxy)methyl]tetrahydro-3-furanyl acetate | 13035-61-5 | C13H18O9 | 详情 | 详情 |
| (II) | 39189 | (2R,3S,4R,5S)-4-(acetoxy)-2-[(acetoxy)methyl]-5-chlorotetrahydro-3-furanyl acetate | C11H15ClO7 | 详情 | 详情 | |
| (III) | 39190 | (2R,3R,4R,5R)-4-(acetoxy)-2-[(acetoxy)methyl]-5-isocyanatotetrahydro-3-furanyl acetate | C12H15NO8 | 详情 | 详情 | |
| (IV) | 26657 | O-methyl isourea; [Amino(imino)methoxy]methane | 52328-05-9 | C2H6N2O | 详情 | 详情 |
| (V) | 39191 | (2R,3R,4R,5R)-4-(acetoxy)-2-[(acetoxy)methyl]-5-[([[(E)-amino(methoxy)methylidene]amino]carbonyl)amino]tetrahydro-3-furanyl acetate | C14H21N3O9 | 详情 | 详情 | |
| (VI) | 39192 | (2R,3R,4R,5R)-4-(acetoxy)-2-[(acetoxy)methyl]-5-[4-methoxy-2-oxo-1,3,5-triazin-1(2H)-yl]tetrahydro-3-furanyl acetate | C15H19N3O9 | 详情 | 详情 |