(1S,2R,5R,8R,8aR)-5-[2'-oxo-2'-(4-methylphenyl)ethyl]-1,2,8-trihydroxy-indolizidine | 675624-06-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,5R,8R,8aR)-5-[2'-oxo-2'-(4-methylphenyl)ethyl]-1,2,8-trihydroxy-indolizidine
• 英文别名: (5R)-5-[2'-oxo-2'-(4-methylphenyl)ethyl]swainsonine；1-(4-Methylphenyl)-2-[(1s,2r,5r,8r,8ar)-1,2,8-Trihydroxyoctahydroindolizin-5-Yl]ethanone；2-[(1S,2R,5R,8R,8aR)-1,2,8-trihydroxy-1,2,3,5,6,7,8,8a-octahydroindolizin-5-yl]-1-(4-methylphenyl)ethanone
• CAS: 675624-06-3
• 化学式: C₁₇H₂₃NO₄
• 分子量: 305.374
• InChiKey: APAFVLSHHZZYGV-PVTMVUMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  81
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2R,5R,8R,8aR)-5-[2'-oxo-2'-(4-methylphenyl)ethyl]-1,2,8-trihydroxy-indolizidine 在 Dowex 1X₈ OH^- form 作用下， 以 甲醇 、 水 为溶剂， 生成 (1S,2R,5S,8R,8aR)-5-[2'-oxo-2'-(4-methylphenyl)ethyl]-1,2,8-trihydroxy-indolizidine
  参考文献：
  名称：

  Synthesis of the New Mannosidase Inhibitors, Diversity-Oriented 5-Substituted Swainsonine Analogues, via Stereoselective Mannich Reaction

  摘要：

  5alpha-Substituted swainsonine analogues were synthesized by Mannich reaction of an in situ generated (-)-swainsonine iminium ion intermediate. 5alpha-Substituted swainsonine analogues were epimerized to their 5beta-isomers in protic solvent.

  DOI：

  10.1021/ol049947m
• 作为产物：
  描述：

  在 palladium dihydroxide 盐酸 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 9.0h， 生成 (1S,2R,5R,8R,8aR)-5-[2'-oxo-2'-(4-methylphenyl)ethyl]-1,2,8-trihydroxy-indolizidine
  参考文献：
  名称：

  Synthesis of the New Mannosidase Inhibitors, Diversity-Oriented 5-Substituted Swainsonine Analogues, via Stereoselective Mannich Reaction

  摘要：

  5alpha-Substituted swainsonine analogues were synthesized by Mannich reaction of an in situ generated (-)-swainsonine iminium ion intermediate. 5alpha-Substituted swainsonine analogues were epimerized to their 5beta-isomers in protic solvent.

  DOI：

  10.1021/ol049947m

文献信息

• Structural Investigation of the Binding of 5-Substituted Swainsonine Analogues to Golgi α-Mannosidase II
  作者：Douglas A. Kuntz、Shinichi Nakayama、Kayla Shea、Hitoshi Hori、Yoshihiro Uto、Hideko Nagasawa、David. R. Rose

  DOI：10.1002/cbic.200900750

  日期：2010.3.22

  Reaching for specificity: X‐ray crystallographic data indicates potent 5α‐substituted swainsonine analogues bind in a novel fashion to Golgi α‐mannosidase II by inserting in a water cluster and by forming new hydrophobic interactions. These offer the potential of being extended into the GlcNAc binding site to improve selectivity and reduce harmful side effects.

  达到特异性： X射线晶体学数据表明有效的5α-取代的swainsonine类似物通过插入水簇中并形成新的疏水性相互作用，以新颖的方式与高尔基α-甘露糖苷酶II结合。这些提供了被扩展到GlcNAc结合位点以改善选择性和减少有害副作用的潜力。
• Synthesis of the New Mannosidase Inhibitors, Diversity-Oriented 5-Substituted Swainsonine Analogues, via Stereoselective Mannich Reaction
  作者：Tomoya Fujita、Hideko Nagasawa、Yoshihiro Uto、Toshihiro Hashimoto、Yoshinori Asakawa、Hitoshi Hori

  DOI：10.1021/ol049947m

  日期：2004.3.1

  5alpha-Substituted swainsonine analogues were synthesized by Mannich reaction of an in situ generated (-)-swainsonine iminium ion intermediate. 5alpha-Substituted swainsonine analogues were epimerized to their 5beta-isomers in protic solvent.