(2S,3R,6R)-6-isopropoxy-2-methyl-3-(propa-1,2-dien-1-yloxy)tetrahydro-2H-pyran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (2S,3R,6R)-6-isopropoxy-2-methyl-3-(propa-1,2-dien-1-yloxy)tetrahydro-2H-pyran
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: LLSWMOUSJWNLAT-QJPTWQEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R,6R)-6-isopropoxy-2-methyl-3-(propa-1,2-dien-1-yloxy)tetrahydro-2H-pyran 在 Grubbs catalyst first generation 、 (S,S)-DACH-phenyl Trost ligand 、 tris-(dibenzylideneacetone)dipalladium(0) 、 三甲胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 22.0h， 生成 (2S,6R)-6-(((2S,3R,6R)-6-isopropoxy-2-methyltetrahydro-2H-pyran-3-yl)oxy)-2-methyl-3,6-dihydro-2Hpyran
  参考文献：
  名称：

  钌催化的二氢吡喃乙缩醛的区域选择性烯烃迁移：从头开始向β-2,6-Dideoxypyranoglycosides的策略。

  摘要：

  在这里，我们报道了针对β-2,6-dideoxypyranoglycosides的从头合成策略。关键事件是二氢吡喃烯丙基乙缩醛向均烯丙基缩醛的钌催化的区域选择性烯烃迁移。结合其他金属催化的反应，该新方案导致以高效方式合成β-2,6-二脱氧吡喃葡萄糖苷。使用这种顺序的金属催化，制备了β-2，6-二脱氧吡喃葡萄糖苷的各种单糖，二糖和三糖形式。

  DOI：

  10.1021/acs.orglett.0c00279
• 作为产物：
  描述：

  (2S,3R,6R)-6-isopropoxy-2-methyl-3-(prop-2-yn-1-yloxy)tetrahydro-2H-pyran 在 potassium tert-butylate 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以78%的产率得到(2S,3R,6R)-6-isopropoxy-2-methyl-3-(propa-1,2-dien-1-yloxy)tetrahydro-2H-pyran
  参考文献：
  名称：

  Pd-Catalyzed Asymmetric Intermolecular Hydroalkoxylation of Allene: An Entry to Cyclic Acetals with Activating Group-Free and Flexible Anomeric Control

  摘要：

  A ligand-directed metal-catalyzed asymmetric intermolecular hydroalkoxylation of alkoxyallene is reported. Combined with ring-closing-metathesis, this reaction offers a new atom-efficient synthetic method toward various cyclic acetals with elaborate anomeric control. Synthetic utility of the reaction was demonstrated by the atom-efficient and stereodivergent access to various mono- and disaccharides.

  DOI：

  10.1021/ja508587f

文献信息

• METHODS FOR THE STEREOSELECTIVE PREPARATION OF APIOSE DERIVATIVES FROM ALLYLIC ALCOHOL COMPOUNDS AND ALLENE COMPOUNDS USING CATALYTIC ASYMMETRIC SYNTHESIS
  申请人：POSTECH ACADEMY-INDUSTRY FOUNDATION

  公开号：US20170369519A1

  公开（公告）日：2017-12-28

  The present invention relates to a method for the stereoselective preparation of apiose derivatives from allylic alcohol compounds and allene compounds using catalytic asymmetric synthesis. The method for the stereoselective preparation of apiose derivatives of the present invention is based on the catalytic asymmetric synthesis from allylic alcohol compounds and allene compounds in the presence of a metal catalyst, so that apiose derivatives can be produced stereoselectively, with high yield, with high optical purity regardless of the types of substituents of the compounds. The method of the invention can also be used for the preparation of oligosaccharides including monosaccharides, disaccharides, and polysaccharides or various compounds including apiose derivatives because the method can minimize the production of by-products without using an activating group, unlike the conventional method for the preparation of adipose derivatives.

  本发明涉及一种从烯丙醇化合物和联苯化合物中使用催化不对称合成的方法，用于立体选择性制备阿匹酮衍生物。本发明的阿匹酮衍生物立体选择性制备方法基于金属催化剂存在下的烯丙醇化合物和联苯化合物的催化不对称合成，因此无论化合物的取代基类型如何，都可以高产率、高光学纯度地立体选择性地产生阿匹酮衍生物。本发明的方法还可用于制备低聚糖，包括单糖、双糖和多糖，或各种化合物，包括阿匹酮衍生物，因为该方法可以最小化副产物的产生，而无需使用活化基，与传统的制备阿匹酮衍生物的方法不同。
• Ruthenium-Catalyzed Regioselective Olefin Migration of Dihydropyran Acetals: A <i>De Novo</i> Strategy toward β-2,6-Dideoxypyranoglycosides
  作者：Kyeongdeok Seo、Young Ho Rhee

  DOI：10.1021/acs.orglett.0c00279

  日期：2020.3.20

  toward β-2,6-dideoxypyranoglycosides. The key event is the ruthenium-catalyzed regioselective olefin migration of dihydropyran allylic acetals to homoallylic acetals. In combination with other metal-catalyzed reactions, this new protocol led to the synthesis of β-2,6-dideoxypyranoglycosides in a highly efficient manner. Using this sequential metal catalysis, various mono-, di-, and trisaccharide forms

  在这里，我们报道了针对β-2,6-dideoxypyranoglycosides的从头合成策略。关键事件是二氢吡喃烯丙基乙缩醛向均烯丙基缩醛的钌催化的区域选择性烯烃迁移。结合其他金属催化的反应，该新方案导致以高效方式合成β-2,6-二脱氧吡喃葡萄糖苷。使用这种顺序的金属催化，制备了β-2，6-二脱氧吡喃葡萄糖苷的各种单糖，二糖和三糖形式。
• Pd-Catalyzed Asymmetric Intermolecular Hydroalkoxylation of Allene: An Entry to Cyclic Acetals with Activating Group-Free and Flexible Anomeric Control
  作者：Wontaeck Lim、Jungjoon Kim、Young Ho Rhee

  DOI：10.1021/ja508587f

  日期：2014.10.1

  A ligand-directed metal-catalyzed asymmetric intermolecular hydroalkoxylation of alkoxyallene is reported. Combined with ring-closing-metathesis, this reaction offers a new atom-efficient synthetic method toward various cyclic acetals with elaborate anomeric control. Synthetic utility of the reaction was demonstrated by the atom-efficient and stereodivergent access to various mono- and disaccharides.