1-(2',3'-Anhydro-5'-deoxy-4',5'-didehydro-α-L-erythro-pentofuranosyl)uracil | 250727-35-6

• 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-4',5'-didehydro-α-L-erythro-pentofuranosyl)uracil
• 英文别名: 1-(2,3-anhydro-5-deoxy-4,5-didehydro-α-L-erythro-pent-4-enofuranosyl)uracil；1-[(1S,2R,5R)-4-methylidene-3,6-dioxabicyclo[3.1.0]hexan-2-yl]pyrimidine-2,4-dione
• CAS: 250727-35-6
• 化学式: C₉H₈N₂O₄
• 分子量: 208.174
• InChiKey: GUHDUSXDDKKZPB-BIIVOSGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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-4',5'-didehydro-α-L-erythro-pentofuranosyl)uracil 在 硼烷 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 1-(3-O-methyl-α-L-xylo-furanosyl)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
• 作为产物：
  描述：

  1-(2,3-anhydro-5-deoxy-5-iodo-β-D-lyxofuranosyl)uracil 在 lithium hexamethyldisilazane 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以92%的产率得到1-(2',3'-Anhydro-5'-deoxy-4',5'-didehydro-α-L-erythro-pentofuranosyl)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

• Regioselective modification of the sugar moiety in pyrimidine nucleosides via a 4′,5′-dehydro-2′,3′-anhydrouridine intermediate
  作者：Kosaku Hirota、Hideki Takasu、Yoshie Tsuji、Hironao Sajiki

  DOI：10.1039/a905608d

  日期：——

  3′-Substituted pyrimidine nucleoside derivatives are obtained in moderate to high yields by the reactionof 1-(2′,3′-anhydro-5′-deoxy-4′,5′-didehydro-α-L-erythro-pentofuranosyl)uracil with nucleophiles without the formation of the corresponding 2′-adduct.

  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。
• Rearrangement of allylic azide and phenylthio groups of 3′-azido- or 3′-phenylthio-4′,5′-didehydro-5′-deoxyarabinofuranosyluridines
  作者：Hideki Takasu、Yoshie Tsuji、Hironao Sajiki、Kosaku Hirota

  DOI：10.1016/j.tet.2005.08.092

  日期：2005.11

  reversible intramolecular [3,3]-sigmatropic rearrangement between 1-(3-azido-3,5-dideoxy-β-d-threo-pent-4-enofuranosyl)uracil (3) and 1-(5-azido-3,5-dideoxy-β-d-glycero-pent-4-enofuranosyl)uracil (4) and irreversible radical rearrangement of 1-(3,5-dideoxy-3-phenylthio-β-d-threo-pent-4-enofuranosyl)uracil (5) and 1-[3,5-dideoxy-3-(4-tolyl)thio-β-d-threo-pent-4-enofuranosyl]uracil (7) into 1-(3,5-dide

  1-（3-azido-3,5 -dideoxy -β-d- threo -pent-4-enofuranosyl）uracil（3）和1-（5-azido-3）之间的可逆分子内[3,3]-σ重排，5-二甲氧基-β-d-甘油-戊-4-烯呋喃糖基）尿嘧啶（4）和1-（3,5-二甲氧基-3-苯硫基-β-d-苏-戊-4-戊呋喃糖基）的不可逆自由基重排）尿嘧啶（5）和1- [3,5-二甲氧基-3-（4-甲苯基）硫代-β-d-苏-戊-4-烯呋喃糖基]尿嘧啶（7）成1-（3,5-二甲氧基- 5-苯硫基-β-1-甘油-戊-4-烯呋喃糖基）尿嘧啶（6）和1- [3,5-二甲氧基-5-（4-甲苯基）硫代-β-1-甘油-戊-3-烯呋喃糖基尿嘧啶（8）是在室温下达到的。
• 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.