(4S,5R,6R)-5,6-epoxyhept-1-en-4-ol | 157968-91-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5R,6R)-5,6-epoxyhept-1-en-4-ol
• 英文别名: (1S)-1-[(2R,3R)-3-methyloxiran-2-yl]but-3-en-1-ol
• CAS: 157968-91-7
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: HWQJBKYWCZLOSU-VQVTYTSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S,5R,6R)-5,6-epoxyhept-1-en-4-ol 在 盐酸 、 二甲基硫 、 臭氧 作用下， 以 四氢呋喃 为溶剂， 生成 (3aR,4R,6S,7aS)-6-methoxy-4-methyl-4,6,7,7a-tetrahydro-3aH-[1,3]oxathiolo[4,5-c]pyran-2-one
  参考文献：
  名称：

  A stereochemically general synthesis of methyl 2,4,6-trideoxy-4-methylthio-α-D-ribo-pyranoside, the thio sugar of esperamicin A1

  摘要：

  A stereochemically general synthesis of methyl 2,4,6-trideoxy-4-methylthio-alpha-D-ribo-pyranoside (1b), the thio sugar isolated from esperamicin, is described. The synthesis involves the neighboring group assisted delivery of a sulfur nucleophile to C(5) of epoxyalcohol 6 via aniline promoted cyclization of thioimidazolide 7.

  DOI：

  10.1016/s0040-4039(00)73285-0
• 作为产物：
  描述：

  (4R,5R,6R)-5,6-epoxyhept-1-en-4-ol 在 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 、 对硝基苯甲酸 作用下， 生成 (4S,5R,6R)-5,6-epoxyhept-1-en-4-ol
  参考文献：
  名称：

  A stereochemically general synthesis of methyl 2,4,6-trideoxy-4-methylthio-α-D-ribo-pyranoside, the thio sugar of esperamicin A1

  摘要：

  A stereochemically general synthesis of methyl 2,4,6-trideoxy-4-methylthio-alpha-D-ribo-pyranoside (1b), the thio sugar isolated from esperamicin, is described. The synthesis involves the neighboring group assisted delivery of a sulfur nucleophile to C(5) of epoxyalcohol 6 via aniline promoted cyclization of thioimidazolide 7.

  DOI：

  10.1016/s0040-4039(00)73285-0

文献信息

• Synthesis and Structure-Activity Relationship of Vicenistatin, a Cytotoxic 20-Membered Macrolactam Glycoside
  作者：Hayato Fukuda、Yuko Nishiyama、Shiina Nakamura、Yutaro Ohno、Tadashi Eguchi、Yoshiharu Iwabuchi、Takeo Usui、Naoki Kanoh

  DOI：10.1002/asia.201200615

  日期：2012.12

  generate the desired 20‐membered macrolactam. This second‐generation strategy made it possible to prepare synthetic analogues of vicenistatin, including the C20‐ and/or C23‐demethyl analogues. Evaluation of the cytotoxic effect of these analogues indicated the importance of the fixed conformation of aglycon for determining the biological activity of the vicenistatins.

  我们已经开发了维斯他汀及其类似物的两种合成物。我们的第一代策略包括通过在C3–C13片段与C1–C2，C14–C19片段之间进行分子间的Horner–Wadsworth–Emmons反应，快速顺序地组装大环内酰胺，然后进行分子内Stille偶联反应。第二代策略利用己烯中间体的闭环复分解反应生成所需的20元大环内酰胺。第二代策略使制备维斯他汀的合成类似物成为可能，包括C20-和/或C23-去甲基类似物。对这些类似物的细胞毒性作用的评估表明，糖苷配基的固定构象对于测定反尼他汀的生物活性很重要。
• Concise Total Synthesis of Vicenistatin
  作者：Naoki Kanoh、Hayato Fukuda、Shiina Nakamura、Tadashi Eguchi、Yoshiharu Iwabuchi

  DOI：10.1055/s-0030-1258574

  日期：2010.10

  A highly convergent total synthesis of macrocyclic lactam glycoside vicenistatin is described. Key features of the synthesis include rapid assembly of the macrolactam part and macrocyclic ring closure via intramolecular Stille coupling.

  描述了大环内酰胺糖苷维尼他汀的高度收敛全合成。该合成的主要特点包括大环内酰胺部分的快速组装和通过分子内 Stille 偶联实现大环闭环。
• Asymmetric synthesis of the hydroxylamino sugar of calicheamicin
  作者：William R. Roush、Bruce C. Follows

  DOI：10.1016/s0040-4039(00)73286-2

  日期：1994.7

  for the conversion of 2,3-epoxyalcohols to N-alkoxy oxazolidinones via the DBU promoted cyclizations of 2,3-epoxy-N-alkoxyurethanes has been developed and applied to the first asymmetric synthesis of the calicheamicin hydroxylamino sugar, 7.

  已经开发了通过DBU促进2,3-环氧-N-烷氧基氨基甲酸酯环化反应将2,3-环氧醇转化为N-烷氧基恶唑烷酮的立体化学通用方法，并将其应用于加利车霉素羟氨基糖的首次不对称合成7。
• A stereochemically general synthesis of methyl 2,4,6-trideoxy-4-methylthio-α-D-ribo-pyranoside, the thio sugar of esperamicin A1
  作者：William R. Roush、Darin Gustin

  DOI：10.1016/s0040-4039(00)73285-0

  日期：1994.7

  A stereochemically general synthesis of methyl 2,4,6-trideoxy-4-methylthio-alpha-D-ribo-pyranoside (1b), the thio sugar isolated from esperamicin, is described. The synthesis involves the neighboring group assisted delivery of a sulfur nucleophile to C(5) of epoxyalcohol 6 via aniline promoted cyclization of thioimidazolide 7.