2',3'-O-cyclohexylidene-5-methyluridine | 1191255-79-4

• 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: 2',3'-O-cyclohexylidene-5-methyluridine
• 英文别名: 1-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)spiro[3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-2,1'-cyclohexane]-4-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1191255-79-4
• 化学式: C₁₆H₂₂N₂O₆
• 分子量: 338.36
• InChiKey: XLFBLCSCBPUEBH-HKUMRIAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  97.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2',3'-O-cyclohexylidene-5-methyluridine 在 碳酸氢钠 、 戴斯-马丁氧化剂 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 1-((3a′S,6′R,6a′R)-4′,4′-bis(hydroxymethyl)tetrahydrospiro-[cyclohexane-1,2′-furo[3,4-d]-[1,3]dioxol]-6′-yl)-5-methylpyrimidine-2,4((1H,3H)-dione)
  参考文献：
  名称：

  Alternative Syntheses of (S)-cEt-BNA: A Key Constrained Nucleoside Component of Bioactive Antisense Gapmer Sequences

  摘要：

  Approaches to the synthesis of the constrained 5-methyluracil nucleoside (S)-cEt-BNA, a key "gapmer" unit in a number of biologically relevant antisense oligonucleotides, are described using 5-methyluridine as starting material. In the shorter synthesis, a nine-step linear sequence afforded a O-protected (S)-cEt-BNA consisting of a [2.2.1]dioxabicycloheptane core in 7% overall yield. A competing reaction in an intramolecular cyclization of a tosylate led to a bicyclic oxetane.

  DOI：

  10.1021/jo502320y
• 作为产物：
  描述：

  环己酮二甲缩酮 、 5-甲基尿甙 在 对甲苯磺酸 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以92%的产率得到2',3'-O-cyclohexylidene-5-methyluridine
  参考文献：
  名称：

  PROCESS FOR PRODUCTION OF ETHYNYLTHYMIDINE COMPOUND USING 5-METHYLURIDINE AS STARTING RAW MATERIAL

  摘要：

  公开号：

  EP2277878B1

文献信息

• PROCESS FOR PRODUCTION OF ETHYNYLTHYMIDINE COMPOUND USING 5-METHYLURIDINE AS STARTING RAW MATERIAL
  申请人：Hamari Chemicals, Ltd.

  公开号：EP2277878B1

  公开（公告）日：2014-09-17
• PRODUCTION PROCESS OF ETHYNYLTHYMIDINE COMPOUNDS FROM 5-METHYLURIDINE AS A STARTING MATERIAL
  申请人：Sato Tatsunori

  公开号：US20110054164A1

  公开（公告）日：2011-03-03

  The present invention provides a process for producing 2′,3′-didehydro-3′-deoxy-4′-ethynylthymidine, which is useful as a medicine, in an efficient and industrially advantageous manner, and more specifically, provides a process for producing 2′,3′-didehydro-3′-deoxy-4′-ethynylthymidine as shown below. (wherein R 1 and R 2 independently represent a protective group for a hydroxy group, or R 1 and R 2 together form a protective group for two hydroxy groups, R 3 and R 4 independently represent a protective group for a hydroxy group, R 5 represents a protective group for a hydroxy group, R 6 represents a protective group for a hydroxy group, X represents a leaving group, and Y represents a halogen atom.)
• US8445669B2
  申请人：——

  公开号：US8445669B2

  公开（公告）日：2013-05-21
• Alternative Syntheses of (<i>S</i>)-cEt-BNA: A Key Constrained Nucleoside Component of Bioactive Antisense Gapmer Sequences
  作者：Juan C. Salinas、Michael T. Migawa、Bradley L. Merner、Stephen Hanessian

  DOI：10.1021/jo502320y

  日期：2014.12.5

  Approaches to the synthesis of the constrained 5-methyluracil nucleoside (S)-cEt-BNA, a key "gapmer" unit in a number of biologically relevant antisense oligonucleotides, are described using 5-methyluridine as starting material. In the shorter synthesis, a nine-step linear sequence afforded a O-protected (S)-cEt-BNA consisting of a [2.2.1]dioxabicycloheptane core in 7% overall yield. A competing reaction in an intramolecular cyclization of a tosylate led to a bicyclic oxetane.