(2R,6S)-6-(cyclohexyloxy)-2-methyl-3,6-dihydro-2H-pyran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2R,6S)-6-(cyclohexyloxy)-2-methyl-3,6-dihydro-2H-pyran
• 英文别名: (2R,6S)-6-cyclohexyloxy-2-methyl-3,6-dihydro-2H-pyran
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: BNRRZACROOYLRJ-PWSUYJOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,6S)-6-(cyclohexyloxy)-2-methyl-3,6-dihydro-2H-pyran 在 四氧化锇 、 [RuHCl(CO)(H₂IMes)(PCy₃)] 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 、 丙酮 、 甲苯 为溶剂， 反应 2.0h， 生成 (2R,3S,4S,6R)-6-(cyclohexyloxy)-2-methyltetrahydro-2H-pyran-3,4-diol
  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：

  ((S)-1-((R)-pent-4-en-2-yloxy)allyloxy)cyclohexane 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到(2R,6S)-6-(cyclohexyloxy)-2-methyl-3,6-dihydro-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

• A Stereoselective Access to Cyclic<i>cis</i>-1,2-Amino Alcohols from<i>trans</i>-1,2-Azido Alcohol Precursors
  作者：Dong-gil Kim、Wook Jeong、Won Jong Lee、Soyeong Kang、Han Kyu Pak、Jaiwook Park、Young Ho Rhee

  DOI：10.1002/adsc.201500267

  日期：2015.5.4

  2‐amino alcohols from trans‐1,2‐azido alcohol precursors was developed. The key step is highlighted by the stereoselective reduction of the cyclic α‐alkoxy imines, which could be prepared from the corresponding azides by ruthenium catalysis under photolytic conditions. Remarkably, this unprecedented reaction pathway offers a stereodivergent access to structurally diverse cyclic 1,2‐amino alcohols.

  从反式1,2-叠氮基醇的前体开发了一种独特的一锅法合成环状顺式1,2-氨基醇。环状α-烷氧基亚胺的立体选择性还原突显了关键步骤，这可以通过在光解条件下通过钌催化由相应的叠氮化物制备。值得注意的是，这种空前的反应途径提供了结构多样的环状1,2-氨基醇的立体异构途径。
• Ru-Catalyzed Chemoselective Olefin Migration Reaction of Cyclic Allylic Acetals to Enol Acetals
  作者：Kyeongdeok Seo、Ye ji Kim、Young Ho Rhee

  DOI：10.1021/acs.orglett.7b03900

  日期：2018.2.16

  A Ru-catalyzed olefin migration reaction of chiral cyclic allylic acetal is reported. The reaction generates cyclic enol acetal in a highly chemoselective manner. A variety of O,O- and N,O-acetals participated in the reaction with conservation of the stereochemical integrity of the acetal moiety. The utility of the reaction was demonstrated by the short and protective group-free syntheses of (L)-deoxyribonucleoside

  报道了Ru催化的手性环状烯丙基缩醛的烯烃迁移反应。该反应以高度化学选择性的方式产生环状烯醇缩醛。各种O，O-和N，O-缩醛参与了反应，并保留了缩醛部分的立体化学完整性。反应的效用由（L）-脱氧核糖核苷和β-酰胺糖苷的短而无保护基团的合成证明。
• 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.