methyl (2S,3S,4R)-4-[(2S,4S,6R)-6-[(2R)-2-[tert-butyl(diphenyl)silyl]oxypropyl]-2-phenyl-1,3-dioxan-4-yl]-3-hydroxy-2-methylpentanoate | 1286242-12-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl (2S,3S,4R)-4-[(2S,4S,6R)-6-[(2R)-2-[tert-butyl(diphenyl)silyl]oxypropyl]-2-phenyl-1,3-dioxan-4-yl]-3-hydroxy-2-methylpentanoate
• CAS: 1286242-12-3
• 化学式: C₃₆H₄₈O₆Si
• 分子量: 604.859
• InChiKey: UGYLVTFKVUOCMK-MFEXCCGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.02
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S,3S,4R)-4-[(2S,4S,6R)-6-[(2R)-2-[tert-butyl(diphenyl)silyl]oxypropyl]-2-phenyl-1,3-dioxan-4-yl]-3-hydroxy-2-methylpentanoate 在 四丁基氟化铵 、 溶剂黄146 、 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (2S,3S,4S)-4-((2S,4S,6S)-6-((R)-2-hydroxypropyl)-2-phenyl-1,3-dioxan-4-yl)-3-(methoxymethoxy)-2-methylpentanoate
  参考文献：
  名称：

  Synthetic Studies of Lepranthin, a Lichen-Produced Dimeric Macrolide. Stereoselective Synthesis of a Seco-Acid Based on Stereospecific Epoxide-Opening Reactions

  摘要：

  The stereoselective synthesis of a seco-acid derivative of lepranthin (1), a lichen-produced unique 16-membered dimeric macrolide, is described wherein all asymmetric carbon centers were constructed in a highly stereoselective manner, respectively, by using different epoxide-opening reactions of the alpha,beta-unsaturated gamma,delta-epoxy ester system and an epoxy alcohol derivative as the key steps.[GRAPHICS].

  DOI：

  10.3987/com-10-12106
• 作为产物：
  描述：

  methyl (R,E)-4-((2S,4S,6R)-6-((R)-2-((tert-butyldiphenylsilyl)oxy)propyl)-2-phenyl-1,3-dioxan-4-yl)pent-2-enoate 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium chlorite 、 sodium dihydrogenphosphate dihydrate 、 2-甲基-2-丁烯 、 L-(+)-酒石酸二乙酯 、 碘苯二乙酸 、 copper(l) cyanide 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 生成 methyl (2S,3S,4R)-4-[(2S,4S,6R)-6-[(2R)-2-[tert-butyl(diphenyl)silyl]oxypropyl]-2-phenyl-1,3-dioxan-4-yl]-3-hydroxy-2-methylpentanoate
  参考文献：
  名称：

  Synthetic Studies of Lepranthin, a Lichen-Produced Dimeric Macrolide. Stereoselective Synthesis of a Seco-Acid Based on Stereospecific Epoxide-Opening Reactions

  摘要：

  The stereoselective synthesis of a seco-acid derivative of lepranthin (1), a lichen-produced unique 16-membered dimeric macrolide, is described wherein all asymmetric carbon centers were constructed in a highly stereoselective manner, respectively, by using different epoxide-opening reactions of the alpha,beta-unsaturated gamma,delta-epoxy ester system and an epoxy alcohol derivative as the key steps.[GRAPHICS].

  DOI：

  10.3987/com-10-12106

文献信息

• Synthetic Studies of Lepranthin, a Lichen-Produced Dimeric Macrolide. Stereoselective Synthesis of a Seco-Acid Based on Stereospecific Epoxide-Opening Reactions
  作者：Shinji Nagumo、Masaaki Miyashita、Hisashi Takada、Eiko Yasui、Megumi Mizukami

  DOI：10.3987/com-10-12106

  日期：——

  The stereoselective synthesis of a seco-acid derivative of lepranthin (1), a lichen-produced unique 16-membered dimeric macrolide, is described wherein all asymmetric carbon centers were constructed in a highly stereoselective manner, respectively, by using different epoxide-opening reactions of the alpha,beta-unsaturated gamma,delta-epoxy ester system and an epoxy alcohol derivative as the key steps.[GRAPHICS].