[(2R,3R)-3-[4-(benzyloxy)butyl]oxiran-2-yl]methanol | 99095-30-4

• 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: [(2R,3R)-3-[4-(benzyloxy)butyl]oxiran-2-yl]methanol
• 英文别名: (2R,3R)-3-[4-(benzyloxy)butyl]oxiran-2-ylmethanol；[(2R,3R)-3-(4-phenylmethoxybutyl)oxiran-2-yl]methanol
• CAS: 99095-30-4
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: WRNGITABMIYVKM-ZIAGYGMSSA-N

物化性质

• 沸点：
  353.2±12.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(2R,3R)-3-[4-(benzyloxy)butyl]oxiran-2-yl]methanol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 乙醚 、 乙腈 为溶剂， 生成 (2R,3S)-2-[4-(benzyloxy)butyl]-3-(iodo-methyl)oxirane
  参考文献：
  名称：

  Stereoselective total synthesis of polyketide lactone, (3R,4S,5S,9S)-3,5,9-trihydroxy-4-methylundecanoic acid δ-lactone

  摘要：

  The total synthesis of lactone I has been described. The convergent asymmetric synthesis relies on the use of an Evans' syn-aldol, chain extension with lithio tert-butyl acetate, and the stereoselective reduction of a ketone as the key reactions. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2009.06.008
• 作为产物：
  描述：

  1,5-戊二醇 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 草酰氯 、 sodium hydride 、 二异丁基氢化铝 、 D-(-)-酒石酸二异丙酯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 [(2R,3R)-3-[4-(benzyloxy)butyl]oxiran-2-yl]methanol
  参考文献：
  名称：

  双亲核取代作为可随时获得哌啶生物碱的合成工具（+）-壬基，（+）-β-羟基，（+）-8-乙基去甲酚和（–）-卤代茄碱

  摘要：

  摘要 在本文中，我们报告了通过苄基胺的双亲核取代，将（+）-精氨酸，（+）-β-精氨酸，（+）-8-乙基去甲酚和（-）-卤代茄灵进行立体选择性全合成，这是关键步骤。 在本文中，我们报告了通过苄基胺的双亲核取代，将（+）-精氨酸，（+）-β-精氨酸，（+）-8-乙基去甲酚和（-）-卤代茄灵进行立体选择性全合成，这是关键步骤。

  DOI：

  10.1055/s-0034-1380151

文献信息

• Total Synthesis of (−)-Brevenal: A Concise Synthetic Entry to the Pentacyclic Polyether Core
  作者：Makoto Ebine、Haruhiko Fuwa、Makoto Sasaki

  DOI：10.1021/ol800685c

  日期：2008.6.5

  Total synthesis of (-)-brevenal, a novel marine polycyclic ether natural product, is described. Highly efficient and scalable entries to the AB-ring exo-olefin and the DE-ring enol phosphate and a rapid construction of the C-ring by means of our Suzuki-Miyaura coupling-based strategy realized a concise synthesis of the pentacyclic skeleton of (-)-brevenal. The present synthesis is considerably more

  描述了一种新型海洋多环醚天然产物（-）-brevenal的全合成。通过我们基于Suzuki-Miyaura偶联的策略，AB环外烯烃和DE环烯醇磷酸酯的高效且可扩展的引入以及C环的快速构建实现了（）的五环骨架的简明合成-）-brevenal。本合成比我们以前的合成效率更高（最长的线性序列：从2-脱氧-d-核糖起50步）。
• ASSEMBLY OF THE SOUTHERN MACROCYCLIC HALF OF (+)-SPIRASTRELLOLIDE A THROUGH CYCLIC ACETAL TETHERED RING-CLOSING METATHESIS AND 1,3-ANTI-MUKAIYAMA-ALDOL
  作者：Richard P. Hsung、Yu Tang、Jin-Haek Yang、Jia Liu、Chao-Chao Wang、Ming-Can Lv、Yi-Biao Wu、Xue-Liang Yu、Changhong Ko

  DOI：10.3987/com-12-s(n)54

  日期：——

  We describe herein details of our efforts in syntheses of A-ring and BC-ring of (+)-spirastrellolide A. While the former would constitute a facile 12-step synthetic endeavor starting from 1,5-pentanediol, the latter would showcase a cyclic acetal-tethered ring-closing metathesis [RCM] method that was developed in our lab for de novo synthesis of spiroketals. Constructing the entire Southern Half of the macrocycle would require 1,3-anti-Mukaiyama aldol addition for connecting A-ring and BC-ring specifically at C10 and C11, thereby culminating a 17-step approach for the Southern Macrocyclic Half linearly from (+)-2,3-(O)-iso-propylidene-L-threitol. Also discussed here is the possibility of pursuing a more convergent approach toward the assembly of the Southern Half through first connecting A-ring and C-ring via acetal formation that would first link together the free C13-OH with C17 at the spiro-BC-ring junction. An ensuing application of our cyclic acetal-tethered RCM strategy to close B-ring would adopt this cyclic acetal intermediate.
• Synthesis of the C1–C16 fragment of spirastrellolide A
  作者：Jia Liu、Jin Haek Yang、Changhong Ko、Richard P. Hsung

  DOI：10.1016/j.tetlet.2006.06.067

  日期：2006.8

  Synthesis of the Cl-C16 fragment of spirastrellolide A is described here featuring Sharpless asymmetric epoxidation, an acid promoted O-1,4-addition, and Mukaiyama 1,3-anti-aldol. (c) 2006 Elsevier Ltd. All rights reserved.
• Bisnucleophilic Substitution as a Synthetic Tool for Ready Access to the Piperidine Alkaloids (+)-Connine, (+)-β-Conhydrine, (+)-8-Ethylnorlobelol, and (–)-Halosaline
  作者：Palakodety Krishna、Galla Raju、Kadimi Anitha

  DOI：10.1055/s-0034-1380151

  日期：——

  Abstract Herein we report the stereoselective total synthesis of (+)-connine, (+)-β-conhydrine, (+)-8-ethylnorlobelol, and (–)-halosaline via bisnucleophilic substitution with benzylamine as the key step. Herein we report the stereoselective total synthesis of (+)-connine, (+)-β-conhydrine, (+)-8-ethylnorlobelol, and (–)-halosaline via bisnucleophilic substitution with benzylamine as the key step.

  摘要 在本文中，我们报告了通过苄基胺的双亲核取代，将（+）-精氨酸，（+）-β-精氨酸，（+）-8-乙基去甲酚和（-）-卤代茄灵进行立体选择性全合成，这是关键步骤。 在本文中，我们报告了通过苄基胺的双亲核取代，将（+）-精氨酸，（+）-β-精氨酸，（+）-8-乙基去甲酚和（-）-卤代茄灵进行立体选择性全合成，这是关键步骤。
• Stereoselective total synthesis of polyketide lactone, (3R,4S,5S,9S)-3,5,9-trihydroxy-4-methylundecanoic acid δ-lactone
  作者：Gowravaram Sabitha、Peddabuddi Gopal、Jhillu S. Yadav

  DOI：10.1016/j.tetasy.2009.06.008

  日期：2009.7

  The total synthesis of lactone I has been described. The convergent asymmetric synthesis relies on the use of an Evans' syn-aldol, chain extension with lithio tert-butyl acetate, and the stereoselective reduction of a ketone as the key reactions. (C) 2009 Published by Elsevier Ltd.