(2S,3S)-(+)-7-benzyloxy-2-methylheptane-1,3-diol | 786668-23-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3S)-(+)-7-benzyloxy-2-methylheptane-1,3-diol
• 英文别名: 7-(benzyloxy)-2-methylheptane-1,3-diol；(2S,3S)-2-methyl-7-phenylmethoxyheptane-1,3-diol
• CAS: 786668-23-3
• 化学式: C₁₅H₂₄O₃
• 分子量: 252.354
• InChiKey: XCKWTINERZQPLA-ZFWWWQNUSA-N

物化性质

• 沸点：
  400.5±40.0 °C(Predicted)
• 密度：
  1.051±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S)-(+)-7-benzyloxy-2-methylheptane-1,3-diol 在 palladium on activated charcoal 咪唑 、 4-二甲氨基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 锂硼氢 、 2-甲基-2-丁烯 、 氢气 、 sodium hexamethyldisilazane 、 三甲基乙酰氯 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 30.67h， 生成 ethyl (4R,7S,8S)-7,9-bis[[tert-butyl(dimethyl)silyl]oxy]-3-hydroxy-4,8-dimethylnonanoate
  参考文献：
  名称：

  Studies directed towards the synthesis of antascomicin A: stereoselective synthesis of the C1–C21 fragment of the molecule

  摘要：

  A stereoselective synthesis of the C1-C21 fragment of the non-immuno suppressive immunophilin-binding natural product, antascomicin A was achieved using, as key steps, highly stereoselective Aldol reactions to build the C1-C17 fragment and a Nozaki-Hiyama-Kishi reaction to couple it with the remaining C18-C21 moiety. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.113
• 作为产物：
  描述：

  5-苄氧基-1-戊醇 在 草酰氯 、 sodium hydride 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 、 间氯过氧苯甲酸 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 11.5h， 生成 (2S,3S)-(+)-7-benzyloxy-2-methylheptane-1,3-diol
  参考文献：
  名称：

  Access to Both Anomers of Pectenotoxin Spiroketals by Kinetic Spiroketalization

  摘要：

  A concise synthesis of both AB ring spiroisomers of the pectenotoxins is described. The nonanomeric AB spiroketal ring system of the pectenotoxins-1, -2, -3, and -6 is formed under very mild, kinetic spiroketalization conditions, along with the anomeric isomer. Only catalytic asymmetric transformations were used as the source of chirality in the synthesis route.

  DOI：

  10.1021/ol048321t

文献信息

• Synthesis of the ABC tricyclic fragment of the pectenotoxins via stereocontrolled cyclization of a γ-hydroxyepoxide appended to the AB spiroacetal unit
  作者：Rosliana Halim、Margaret A. Brimble、Jörn Merten

  DOI：10.1039/b600951d

  日期：——

  spiroacetal fragment was achieved via addition of acetylene 11 to the unstable allylic iodide 39. Epoxidation of (E)-enyne 8 via in situ formation of L-fructose derived dioxirane generated the desired syn-epoxide 36. Semi-hydrogenation of the resulting epoxide 36 followed by dihydroxylation of the alkene effected concomitant cyclization, thus completing the synthesis of the ABC spiroacetal ring fragment

  已经完成了含有C1-C16 ABC螺缩醛的果胶毒素7 6的三环片段的立体控制合成。关键的AB螺缩醛醛9是通过酸催化环化的容易由醛12和砜13制备的受保护的酮前体28合成的。醛12中的顺式立体化学是通过烯醇钛进行的不对称羟醛反应进行安装的。砜13中的立体异构中心来源于（R）-（+）-缩水甘油。最终的螺缩醛醛9的绝对立体化学通过NOE研究证实，确定了螺缩醛中心的（S）-立体化学。
• Synthesis of the ABC Fragment of the Pectenotoxins
  作者：Rosliana Halim、Margaret A. Brimble、Jörn Merten

  DOI：10.1021/ol0507975

  日期：2005.6.1

  [reaction: see text] A highly stereocontrolled synthesis of the C1-C16 ABC spiroacetal-containing fragment 5 of PTX7 (4) has been achieved. Appendage of the C ring to the AB fragment involved Wittig reaction of spiroacetal aldehyde 8 with a stabilized ylide 9 followed by displacement of allylic iodide 27 with a lithium acetylide to afford enyne 7. Fructose-derived chiral dioxirane and dihydroxylation

  [反应：见正文]已经实现了PTX7的C1-C16 ABC含螺缩醛的片段5的高度立体控制的合成（4）。C环与AB片段的连接涉及螺缩醛8与稳定的内酯9的Wittig反应，然后用乙炔化锂置换碘代烯丙基碘27以得到烯炔7。然后使用果糖衍生的手性二环氧乙烷和二羟基化反应引入四氢呋喃C环中正确的官能团。
• Access to Both Anomers of Pectenotoxin Spiroketals by Kinetic Spiroketalization
  作者：Petri M. Pihko、Jatta E. Aho

  DOI：10.1021/ol048321t

  日期：2004.10.1

  A concise synthesis of both AB ring spiroisomers of the pectenotoxins is described. The nonanomeric AB spiroketal ring system of the pectenotoxins-1, -2, -3, and -6 is formed under very mild, kinetic spiroketalization conditions, along with the anomeric isomer. Only catalytic asymmetric transformations were used as the source of chirality in the synthesis route.
• Studies directed towards the synthesis of antascomicin A: stereoselective synthesis of the C1–C21 fragment of the molecule
  作者：Tushar Kanti Chakraborty、Bajjuri Krishna Mohan

  DOI：10.1016/j.tetlet.2006.05.113

  日期：2006.7

  A stereoselective synthesis of the C1-C21 fragment of the non-immuno suppressive immunophilin-binding natural product, antascomicin A was achieved using, as key steps, highly stereoselective Aldol reactions to build the C1-C17 fragment and a Nozaki-Hiyama-Kishi reaction to couple it with the remaining C18-C21 moiety. (c) 2006 Elsevier Ltd. All rights reserved.