1-(2,3-anhydro-5-deoxy-5-iodo-β-D-lyxofuranosyl)uracil | 84365-08-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(2,3-anhydro-5-deoxy-5-iodo-β-D-lyxofuranosyl)uracil
• 英文别名: 1-[(1S,2R,4S,5R)-4-(iodomethyl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl]pyrimidine-2,4-dione
• CAS: 84365-08-2
• 化学式: C₉H₉IN₂O₄
• 分子量: 336.086
• InChiKey: NIHYHYPHWUTHRV-YDKYIBAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  71.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2,3-anhydro-5-deoxy-5-iodo-β-D-lyxofuranosyl)uracil 在 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 1-(3,5-dideoxy-5-phenylthio-α-L-glycero-pent-3-enofuranosyl)uracil
  参考文献：
  名称：

  Regioselective modification of the sugar moiety in pyrimidine nucleosides via a 4′,5′-dehydro-2′,3′-anhydrouridine intermediate

  摘要：

  通过 1-(2â²,3â²-anhydro-5â²-deoxy-4â²,5â²-didehydro-δ-±-L-erythro-pentofuranosyl)uracil 与亲核物反应，可获得中等至高产率的 3â²-取代嘧啶核苷衍生物，且不会形成相应的 2â²-加合物。

  DOI：

  10.1039/a905608d

文献信息

• Biomolecules Bearing the SAsMe2 Group: Nucleoside Derivatives
  作者：Norbert L. M. Dereu、Ralph A. Zingaro

  DOI：10.1002/bscb.19820910804

  日期：——

  AbstractA number of compounds of the type GS‐ and GSeAsR2, where G is a monosaccharide, a thio amino acid, a thiol‐containing di‐ or tripeptide or cholesterol display carcinostatic activity in in vivo mouse test systems.The synthesis and characterization of derivatives in which G is a nucleoside and the synthesis of an arsenic‐containing precursor of 5‐thioglucose are described. Of the nucleoside derivatives thus far screened, none displays carcinostatic activity.
• 3′-Selective modification of a 4′,5′-didehydro-5′-deoxy-2′,3′-epoxyuridine using nucleophiles
  作者：Hideki Takasu、Yoshie Tsuji、Hironao Sajiki、Kosaku Hirota

  DOI：10.1016/j.tet.2005.06.053

  日期：2005.8

  1-(2,3-Anhydro-5-deoxy-4,5-didehydro-alpha-(L)-erythro-pent-4-enofuranosyl)uracil 4 was obtained by the treatment of 5 '-iodo-2 ',3 '-epoxyuridine 5 with LiHMDS in excellent yield. The pyrimidine nucleoside 4 possesses quite unique vinyl epoxide moiety within the molecules. The reactions of 4 with a variety of nucleophiles gave 3 '-substituted pyrimidine nucleosides without the formation of the corresponding 2 '-substituted isomers. In the case of NaN3 or PhSH, the corresponding 5 '-adduct was obtained as a minor product together with the expected 3 '-adduct. (c) 2005 Elsevier Ltd. All rights reserved.
• Formation of 4’,5’-Didehydro-5’-deoxy-3’-O-methyluridine via Regioselective Nucleophilic Addition of Methoxide Anion to 2’,3’-Anhydro-5’-dehydro-5’-iodouridine
  作者：Hironao Sajiki、Hideki Takasu、Kosaku Hirota

  DOI：10.3987/com-05-s(t)14

  日期：——

  Treatment of 2',3'-anhydro-5'-deoxy-5'-iodouracil (1) with sodium methoxide regioselectively provided 4',5'-didehydro-5'-deoxy-3'-O-methyl-uridine (2) as the sole product via 4',5'-didehydro-5'-deoxy-2',3'-epoxyuridine (6) as an intermediate.
• Reactivity of 2',3'-Anhydro Pyrimidine Nucleosides toward Trimethylaluminum
  作者：Kosaku Hirota、Hideki Takasu、Hironao Sajiki

  DOI：10.3987/com-99-s144

  日期：——

  Treatment of 2',3'-anhydro pyrimidine nucleoside derivatives (1) with trimethylaluminum afforded 1-(3-deoxy-3-methyl-beta-D-arabinofuranosyl)pyrimidine derivatives (2) and 1-(2-deoxy-2-methyl-beta-D-xylofuranosyl)pyrimidine derivatives (3) as a mixture in approximately 2 : 1 - 3 : 1 ratio via ring-opening of the epoxide involving the nucleophilic attack of trimethylaluminum at the 3' or 2'-position of 1.