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題名 | Studies on the Stereoselective Synthesis of 3'-Deoxy-3'-α-N-hydroxy-N-methylamino-D-thymidine Using (S)-5-(Triphenylmethoxy-methyl)-2(5H)-furanone as the Starting Material=氮-氫氧基-氮-甲胺基-去氧胸甘的合成研究 |
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作 者 | 楊德芳; 詹家鼎; 張竣評; 簡芳祺; 鍾芬裕; | 書刊名 | 朝陽學報 |
卷期 | 5 2000.08[民89.08] |
頁次 | 頁91-101 |
分類號 | 346.01 |
關鍵詞 | 三苯基-甲氧基-甲基內酯; 甲胺基-3'-去氧胸甘; 醣化反應; (Triphenylmethoxy)methyl-γ-butyrolactone; Methylamino-D-thymidine; Glycosilation reaction; |
語文 | 英文(English) |
中文摘要 | 首先,以5-(三苯基-甲氧基-甲基)-2,3-不飽合內酯(化合物4)做為起始物,與氮-氫氧基-甲基氨進行共軛加成反應,生成3'-氮-氫氧基-氮-甲胺基內酯(化合物5)。接著,進行氫氧基的保護反應、內酯的還原反應及乙醯化反應,而生成乙醯化內醇(化合物8)中間體。此中間體再經過化反應,產生帶有保護基的各種3'-去氧甘衍生物及異構物(化合物9,10,11,12)。最後,這些衍生物及異構物進行去保護反應,而生成目標物(3'-氮-氫氧基-氮-甲胺基-3'-去氧胸甘)。此目標產物為二個立體異構物(化合物2a,3),而其立體構型則分別為經由核磁共振光譜儀偵測加以確定。 |
英文摘要 | Conjugate addition reaction of (S)-(-)-5-(triphenylmethoxy-methy1)-2(5H)-furanone (compound 4) with N-methyl hydroxylamine provided β-(R)-(N-hydroxy-N-methyl) amino-γ-(S)-(triphenylmethoxy) methyl-γ-butyrolactone (compound 5). Protection of hydroxyl group on nitrogen atom of compound 5 followed by treatment of the lactone with DIBAL-H gave a lactol (compound 7), which immediately underwent acetylation reaction and afforded 1-O-Acetyl-5-O-triphenylmethyl-2, 3-dideoxy-3-(N-tert-butyldimethylsiloxy-N-methyl)-amino α-and-β-D-erythro-pentofuranose (compound 8). Glycosilation reaction of compound 8 with silylated thymine gave a mixture of four components, including 5'-O-trityl-3'-deoxy-3'-α-N-tert-butyldimethylsiloxy-N-methyl) amino-α-and-β-D-thymidines (compounds 9 and 10) and 3'-doxy-3'-α-N-tert-butyldimethylsiloxy-N-methyl) amino-α-and-β-D-thymidines (compounds 11 and 12). Removal of the protecting groups on compounds 9-12 provided the target products (compounds 2a and 3). |
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