(3R,4S,5R,6S)-1-thia-spiro[4,4]nonane-3,4,6-triol | 862080-75-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: (3R,4S,5R,6S)-1-thia-spiro[4,4]nonane-3,4,6-triol
• 英文别名: (3R,4S,5R,9S)-1-thiaspiro[4.4]nonane-3,4,9-triol
• CAS: 862080-75-9
• 化学式: C₈H₁₄O₃S
• 分子量: 190.263
• InChiKey: KIJLBEKXAVEUNG-DKXJUACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  86
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R,6S)-1-thia-spiro[4,4]nonane-3,4,6-triol 在 吡啶 、 三乙烯二胺 、 4-二甲氨基吡啶 、 Davis oxaziridine reagent 、 silver nitrate 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 20.0h， 生成 2,4-Dimethoxy-benzoic acid (1R,2R,4R,5S,11S)-7,7,9,9-tetraisopropyl-2-oxo-6,8,10-trioxa-2λ4-thia-7,9-disila-tricyclo[9.3.0.01,5]tetradec-4-yl ester
  参考文献：
  名称：

  Stereoselective Synthesis of β-Anomeric 4‘-Thiaspirocyclic Ribonucleosides Carrying the Full Complement of RNA-Level Hydroxyl Substitution

  摘要：

  Stereoselective syntheses of a group of 4'-thiaspirocyclic ribonucleosides featuring both pyrimidine and purine classes and both possible configurations at C-5' are described. Use is made of the Pummerer reaction of substrates carrying an a-oriented 2,4-dimethoxybenzoyloxy substituent at C-2 in order to gain reliable stereocontrol via neighboring group participation. Irrespective of the S or R configuration of the pivotal sulfoxide intermediates, the nucleobase is captured from the beta-face. The competing process is formation of unsaturated sulfoxides, presumably via competing E2-type elimination. Although differences in reactivity between the two stereoisomeric series were noted, the common route has successfully given rise for the first time to desirable beta-anomeric sulfur-containing spiroribonucleosides with minimum formation of the alpha-anomers.

  DOI：

  10.1021/jo0506985
• 作为产物：
  描述：

  在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以91%的产率得到(3R,4S,5R,6S)-1-thia-spiro[4,4]nonane-3,4,6-triol
  参考文献：
  名称：

  Stereoselective Synthesis of β-Anomeric 4‘-Thiaspirocyclic Ribonucleosides Carrying the Full Complement of RNA-Level Hydroxyl Substitution

  摘要：

  Stereoselective syntheses of a group of 4'-thiaspirocyclic ribonucleosides featuring both pyrimidine and purine classes and both possible configurations at C-5' are described. Use is made of the Pummerer reaction of substrates carrying an a-oriented 2,4-dimethoxybenzoyloxy substituent at C-2 in order to gain reliable stereocontrol via neighboring group participation. Irrespective of the S or R configuration of the pivotal sulfoxide intermediates, the nucleobase is captured from the beta-face. The competing process is formation of unsaturated sulfoxides, presumably via competing E2-type elimination. Although differences in reactivity between the two stereoisomeric series were noted, the common route has successfully given rise for the first time to desirable beta-anomeric sulfur-containing spiroribonucleosides with minimum formation of the alpha-anomers.

  DOI：

  10.1021/jo0506985

文献信息

• Synthesis of aza- and thia-spiroheterocycles and attempted synthesis of spiro sulfonium compounds related to salacinol
  作者：Wang Chen、B. Mario Pinto

  DOI：10.1016/j.carres.2007.07.003

  日期：2007.11

  The synthesis of aza- and thia-spiroheterocycles and the attempted synthesis of spiro sulfonium compounds related to salacinol are described. The binding of the nanomolar inhibitor swainsonine to Drosophila Golgi alpha-mannosidase II (dGMII) involves a large contribution of interactions between the six-membered ring of the inhibitor and the hydrophobic pocket within the enzyme active site. Salacinol

  描述了氮杂-和硫杂-螺杂环的合成以及与salacinol有关的螺sulf化合物的合成尝试。纳摩尔抑制剂swainsonine与果蝇高尔基体α-甘露糖苷酶II（dGMII）的结合涉及抑制剂的六元环与酶活性位点内的疏水口袋之间相互作用的巨大贡献。Salacinol是一种天然存在的sulf离子，是网状S草水提取物中的活性成分之一，该提取物传统上在斯里兰卡和印度用于治疗糖尿病。设计了螺氮杂和硫杂杂环以及salacinol的螺类似物，并期望烃部分对结合起疏水作用。前几套化合物已成功合成，但水杨素类似物却难以捉摸。最终化合物的立体化学是通过1D-NOESY实验确定的。氮杂和硫杂杂环不是高尔基α-甘露糖苷酶II或人麦芽糖酶葡糖淀粉酶的有效抑制剂。