endo-3-benzyloxy-endo,endo-2,4-dimethyl-exo-6-hydroxy-8-oxabicyclo[3.2.1]octane | 171231-72-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: endo-3-benzyloxy-endo,endo-2,4-dimethyl-exo-6-hydroxy-8-oxabicyclo[3.2.1]octane
• 英文别名: (1R,2S,3S,4S,5R,6S)-2,4-dimethyl-3-phenylmethoxy-8-oxabicyclo[3.2.1]octan-6-ol
• CAS: 171231-72-4
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: NGZCIIGSNOAORM-HGWSZMDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  endo-3-benzyloxy-endo,endo-2,4-dimethyl-exo-6-hydroxy-8-oxabicyclo[3.2.1]octane 在 lithium aluminium tetrahydride 、 camphor-10-sulfonic acid 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 (2R,3R,4S)-3-(benzyloxy)-4-((R)-2,2-dimethyl-1,3-dioxan-4-yl)-2-methylpentan-1-ol
  参考文献：
  名称：

  A stereoconvergent synthesis of the C(19)C(31) fragment of scytophycin C

  摘要：

  The C(19)-C(31) fragment of the anti-tumor macrolide, scytophycin C, was realized in a stereoconvergent manner utilizing a desymmetrization approach to create eight contiguous asymmetric centers from a common precursor. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01705-7
• 作为产物：
  描述：

  (1R,2R,3r,4S,5S)-2,4-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-ol 在 sodium hydroxide 、 dimethyl sulfide borane 、 双氧水 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 endo-3-benzyloxy-endo,endo-2,4-dimethyl-exo-6-hydroxy-8-oxabicyclo[3.2.1]octane
  参考文献：
  名称：

  利福霉素-S的C-19至C-27片段的不对称合成

  摘要：

  描述了由Ipc 2 BH作为手性氢硼化试剂组成的由7个连续的不对称中心组成的利福霉素S的C-19至C-27片段的高度立体选择性不对称合成。

  DOI：

  10.1016/0040-4039(95)01571-x

文献信息

• A Stereoselective Synthesis of the C20-C32 Fragment of the Phorboxazoles
  作者：J. Yadav、M. Satyanarayana、G. Srinivasulu、A. Kunwar

  DOI：10.1055/s-2007-982556

  日期：2007.6

  The C20-C32 fragment of the phorboxazoles was ­realized in a stereoconvergent manner utilizing a desymmetrization approach. This successful strategy involves epimerization and ­modified Julia olefination as key steps.

  C20-C32 片段的合成是通过去对称化策略以立体汇聚的方式实现的。这一成功的策略涉及差向异构化和改良的 Julia 烯烃化作为关键步骤。
• Formal Total Synthesis of (−)-Saliniketals
  作者：J. S. Yadav、Sk. Samad Hossain、Madasu Madhu、Debendra K. Mohapatra

  DOI：10.1021/jo901913h

  日期：2009.11.20

  A highly stereoselective formal total synthesis of the ornithine decarboxylase inhibitors (−)-saliniketals A and B is described. The salient features of the synthesis are the utilization of a desymmetrization technique to create six contiguous chiral centers from a single bicyclic precursor as well as substrate-controlled Grignard reaction, intramolecular Wacker-type oxidation, and antialdol reaction

  描述了鸟氨酸脱羧酶抑制剂（-）-盐基酮A和B的高度立体选择性的正式全合成。合成的显着特征是利用去对称化技术从单个双环前体以及在Pirrung-Heathcock条件下受底物控制的格氏反应，分子内Wacker型氧化和抗醛醇缩合反应创建六个连续的手性中心。
• Studies towards the total synthesis of (−)-callystatin A
  作者：J.S. Yadav、K. Yadagiri、Ch. Madhuri、G. Sabitha

  DOI：10.1016/j.tetlet.2011.05.151

  日期：2011.8

  The synthesis of C1–C12 and C13–C22 fragments of (−)-callystatin A is accomplished employing desymmetrization strategy for the creation of five chiral centres of the polypropionate fragment and application of cross-metathesis (CM) reaction for the first time for this molecule.

  （-）-callystatin A的C 1 –C 12和C 13 –C 22片段的合成采用去对称化策略创建了聚丙烯酸酯片段的五个手性中心，并应用了交叉复分解（CM）反应第一次为这个分子。
• Synthesis of C15–C27 segment of venturicidine X by utilizing desymmetrization protocol
  作者：J.S. Yadav、Sk. Samad Hossain、Debendra K. Mohapatra

  DOI：10.1016/j.tetlet.2010.05.148

  日期：2010.8

  We have achieved the synthesis of C15-C27 fragment of venturicidine X using desymmetrization protocol, substrate-controlled Grignard reaction, Barton-McCombie reaction, Sharpless epoxidation, and TBSOTf-mediated rearrangement to produce the aldol product through a non-aldol route as the key step following 23 longest linear sequences with 6.4% overall yield starting from a known intermediate 11. (C) 2010 Elsevier Ltd. All rights reserved.
• Total Synthesis of (-)-Invictolide
  作者：Jhillu Yadav、K. Lakshmi、N. Reddy、Attaluri Prasad、Ahmad Al Khazim Al Ghamdi

  DOI：10.1055/s-0032-1316561

  日期：2012.8

  A convergent approach to the total synthesis of (-)-invictolide, a component of the queen recognition pheromone of Solenopsis invicta, is described. Key steps involve the desymmetrization of a bicyclic olefin with Brown's chiral hydroboration, C-C bond formation, 1,3-syn reduction, and oxidative lactonization of a 1,3,5-triol with TEMPO/PhI(OAc)(2).