((2R,3R)-3-(4-(tert-butyldimethylsilyloxy)butyl)oxiran-2-yl)methanol | 121352-65-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: ((2R,3R)-3-(4-(tert-butyldimethylsilyloxy)butyl)oxiran-2-yl)methanol
• 英文别名: (2R,3R)-3-(4-[(1,1-dimethylethyl)dimethylsilyloxy]butyl)oxirane-2-methanol；[(2R,3R)-3-[4-[tert-butyl(dimethyl)silyl]oxybutyl]oxiran-2-yl]methanol
• CAS: 121352-65-6
• 化学式: C₁₃H₂₈O₃Si
• 分子量: 260.449
• InChiKey: IGOJQDLQJJPACI-VXGBXAGGSA-N

物化性质

• 沸点：
  302.5±7.0 °C(Predicted)
• 密度：
  0.948±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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-(tert-butyldimethylsilyloxy)butyl)oxiran-2-yl)methanol 在 咪唑 、 碘 、 三苯基膦 、 sodium iodide 、 锌 作用下， 以 甲醇 、 乙醚 、 乙腈 为溶剂， 反应 7.0h， 生成 (R)-7-{[1-(tert-Butyl)-1,1-dimethylsilyl]oxy}hept-1-en-3-ol
  参考文献：
  名称：

  通过有机催化不对称合成（+）-甜菊酯C和（-）-aspinolide A

  摘要：

  已经从容易获得的原料中描述了两种重要的真菌代谢物，（+）-斯塔格奈德C和（-）-aspinolide A的新的对映选择性合成。脯氨酸催化的不对称α-氨氧基化和约根森的醛环氧化是引入手性的关键反应。最终通过Steglich酯化反应和闭环易位反应完成了10元内酯核心结构的形成。

  DOI：

  10.1016/j.tetasy.2012.10.007
• 作为产物：
  描述：

  5-((叔丁基二甲基甲硅烷基)氧基)戊醛 在 titanium tetraisopropoxide 、 sodium hydride 、 二异丁基氢化铝 、 D-(-)-酒石酸二异丙酯 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 mineral oil 为溶剂， 反应 68.5h， 生成 ((2R,3R)-3-(4-(tert-butyldimethylsilyloxy)butyl)oxiran-2-yl)methanol
  参考文献：
  名称：

  Synthesis of the PMB Ether of 5,6-Epoxyisoprostane E2 through Aldol Reaction of the α-Bromocyclopentanone

  摘要：

  5,6-Epoxyisoprostane E2 was synthesized via bromohydrination of the cyclopentene and aldol reaction of the alpha-bromocyclopentanone with the epoxyaldehyde. High regioselectivity in the bromohydrination was attained with recrystallized NBS and pyridine in aqueous DMSO. The enolate for the aldol reaction was generated by adding t-BuLi to the mixture of the a-bromocyclopentanone and ZnI2. This aldol protocol was applied successfully to several cyclopentanones and aldehydes.

  DOI：

  10.1021/ol500654g

文献信息

• Asymmetric Total Synthesis of (+)-K01-0509 B:  Determination of Absolute Configuration
  作者：Satoshi Tsuchiya、Toshiaki Sunazuka、Tomoyasu Hirose、Ryuma Mori、Toshiaki Tanaka、Masato Iwatsuki、Satoshi Ōmura

  DOI：10.1021/ol062282z

  日期：2006.11.1

  K01-0509 B is a novel natural product which contains a carbamoylated cyclic guanidine. Our asymmetric total synthesis features a Sharpless asymmetric epoxidation and a stereocontrolled construction of the cyclic guanidine via an asymmetric nitroaldol reaction, followed by intramolecular SN2 cyclization. These reactions allowed the cyclic guanidine and the adjacent hydroxy group to be assembled, facilitating

  K01-0509 B是一​​种新型的天然产物，其中含有氨基甲酰化的环状胍。我们的不对称总合成具有Sharpless不对称环氧化和通过不对称硝基醛缩醛反应进行立体控制的环状胍结构，然后进行分子内SN2环化的​​过程。这些反应使环状胍和相邻的羟基组装，促进了不对称的总合成和K01-0509 B的绝对立体化学的确定。
• Improved Synthesis of the Epoxy Isoprostane Phospholipid PEIPC and its Reactivity with Amines
  作者：Michael E. Jung、Judith A. Berliner、Lukasz Koroniak、B. Gabriel Gugiu、Andrew D. Watson

  DOI：10.1021/ol8014804

  日期：2008.10.2

  An improved synthesis of the naturally occurring hydroxy ketone 1-palmitoyl-2-(5,6)-epoxyisoprostane E-2-sn-glycero-3-phosphocholine (PEIPC) 1, a compound that plays a role in endothelial activation in atherosclerosis, has been carried out using a PMB ether as the key protecting group. Opening of an intermediate with pentylamine shows that the allylic epoxide is the position of attack by nucleophiles.
• A highly stereocontrolled route to 2-(2′-oxiranyl)piperidines and pyrrolidines: enantioselective synthesis of (+)-α-conhydrine
  作者：Dídac Rodríguez、Anna Picó、Albert Moyano

  DOI：10.1016/j.tetlet.2008.09.095

  日期：2008.11

  The first enantio- and diastereoselective approach to both 2-(2'-oxiranyl)piperidines and to 2-(2'-oxiranyl)pyrrolidines is reported. The method relies on the Sharpless asymmetric epoxidation of allyl alcohols as the sole source of chirality, and involves as the key step the base-mediated cyclization of (alpha-aminoalkyl)oxiranes functionalized at the is an element of (or delta) position. The asymmetric synthesis of (+)-alpha-conhydrine illustrates the applicability of this strategy to the preparation of biologically active 2-(1-hydroxyalkyl)piperidine alkaloids. (c) 2008 Elsevier Ltd. All rights reserved.
• Enantioselective total synthesis of the tricyclic 9-oxabispidine (1R,2S,9S)-11-methyl-13-oxa-7,11-diazatricyclo[7.3.1.02,7]tridecane
  作者：Matthias Breuning、Melanie Steiner

  DOI：10.1016/j.tetasy.2008.08.002

  日期：2008.8

  The enantiomerically pure tricyclic 9-oxabispidine (1R,2S,9S)-11-methyl-13-oxa-7,11-diazatricyclo[7.3.1.0(2.7) ]tridecane, a potential substitute for (+)-sparteine in asymmetric synthesis, was prepared in 7 steps and in 11% overall yield from a chiral epoxy alcohol and (S)-epichlorohydrin. The key intermediate was a bicyclic 9-oxabispidine with an appropriately functionalized, endo-oriented side chain. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of the PMB Ether of 5,6-Epoxyisoprostane E2 through Aldol Reaction of the α-Bromocyclopentanone
  作者：Hidehisa Kawashima、Yuichi Kobayashi

  DOI：10.1021/ol500654g

  日期：2014.5.16

  5,6-Epoxyisoprostane E2 was synthesized via bromohydrination of the cyclopentene and aldol reaction of the alpha-bromocyclopentanone with the epoxyaldehyde. High regioselectivity in the bromohydrination was attained with recrystallized NBS and pyridine in aqueous DMSO. The enolate for the aldol reaction was generated by adding t-BuLi to the mixture of the a-bromocyclopentanone and ZnI2. This aldol protocol was applied successfully to several cyclopentanones and aldehydes.