1,2:4,5-di-O-cyclohexylidene-β-D-erythro-hexo-2,3-diulopyranose | 18546-20-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 1,2:4,5-di-O-cyclohexylidene-β-D-erythro-hexo-2,3-diulopyranose
• CAS: 18546-20-8
• 化学式: C₁₈H₂₆O₆
• 分子量: 338.401
• InChiKey: BEUDHKWSFDORKA-LBTNJELSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2:4,5-di-O-cyclohexylidene-β-D-erythro-hexo-2,3-diulopyranose 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 盐酸羟胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 9.5h， 生成 3-amino-3-deoxy-1,2:4,5-di-O-cyclohexylidene-β-D-psycopyranose
  参考文献：
  名称：

  Z-,E-Isomer of 1,2:4,5-di-O-cyclohexylidene-β-d-erythro-hexo-2,3-diulopyranose oxime

  摘要：

  The syntheses of 1,2:4,5-di-O-cyclohexylidene-beta-D-fructopyranose and 1,2:4,5-di-O-cyclohexylidene-beta-D-erythro-hexo-2,3-diulopyranose were improved. A method for the separation of isomeric oximes of diulose was developed, and their structures were established by C-13 NMR spectroscopy. 3-Amino-3-deoxy-1,2:4,5-di-O-cyclohexylidene-beta-D-psycopyranose was obtained.

  DOI：

  10.1007/bf01431332
• 作为产物：
  描述：

  在 3 A molecular sieve pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以90.1%的产率得到1,2:4,5-di-O-cyclohexylidene-β-D-erythro-hexo-2,3-diulopyranose
  参考文献：
  名称：

  Catalytic asymmetric epoxidation

  摘要：

  一种化合物及其生产方法被披露，该方法使用手性酮和氧化剂从烯烃生产具有对映体富集的环氧乙烷。

  公开号：

  US06348608B1
• 作为试剂：
  描述：

  乌非拉唑 在 Oxone 、 乙二胺四乙酸 、 碳酸氢钠 、 1,2:4,5-di-O-cyclohexylidene-β-D-erythro-hexo-2,3-diulopyranose 作用下， 以 乙腈 为溶剂， 反应 3.25h， 生成 奥美拉唑 、 埃索美拉唑
  参考文献：
  名称：

  WO2007/88559

  摘要：

  公开号：

文献信息

• A multipolymer system for organocatalytic alcohol oxidation
  作者：Tracy Yuen Sze But、Yousuke Tashino、Hideo Togo、Patrick H. Toy

  DOI：10.1039/b500965k

  日期：——

  A system involving two polymer-supported reagents for the selective and organocatalytic oxidation of alcohols to aldehydes or ketones has been developed in which both polymeric reagents can be recovered and reused.

  开发了一个涉及两种高分子支持的试剂的系统，用于选择性和有机催化氧化醇类为醛或酮，其中两种高分子试剂均可回收和重复使用。
• Soluble polystyrene-based sulfoxide reagents for Swern oxidation reactions
  作者：Matthew Kwok Wai Choi、Patrick H Toy

  DOI：10.1016/s0040-4020(03)01105-0

  日期：2003.9

  are introduced. These polymeric reagents are used in Swern oxidation reactions where the resulting sulfide polymers are easily separated from the product by simple precipitation and filtration. The recovered reduced polymer reagents can be recycled by oxidation with tert-butyl hydroperoxide in the presence of acid. Attempts to use these reagents in a multi-polymer Swern oxidation reaction system were

  介绍了两种新型的可溶聚苯乙烯基亚砜试剂。这些聚合试剂用于Swern氧化反应中，通过简单的沉淀和过滤，很容易将生成的硫化物聚合物与产物分离。回收的还原的聚合物试剂可以通过在酸的存在下用叔丁基氢过氧化物氧化来再循环。尝试在多元Swern氧化反应系统中使用这些试剂均未成功。
• Polymer-supported thioanisole: a versatile platform for organic synthesis reagents
  作者：Matthew Kwok Wai Choi、Patrick H Toy

  DOI：10.1016/j.tet.2004.01.074

  日期：2004.3

  A new cross-linked polystyrene-supported thioanisole reagent is reported. This reagent incorporates the flexible JandaJel(TM) cross-linker and can be treated with methyl trifluoromethanesulfonate to form the corresponding sulfonium salt. This salt can in turn be deprotonated to form a polymer-supported sulfur ylide that is able to react with aldehydes and ketones to form epoxides. The thioanisole reagent can also be oxidized to form an insoluble sulfoxide reagent that is useful in Swern oxidation reactions. In these reactions, the polymer-supported thioanisole-based reagents can be recovered, regenerated and reused. (C) 2004 Elsevier Ltd. All rights reserved.
• Structural Probing of Ketone Catalysts for Asymmetric Epoxidation
  作者：Yong Tu、Zhi-Xian Wang、Michael Frohn、Mingqi He、Hongwu Yu、Yong Tang、Yian Shi

  DOI：10.1021/jo9817218

  日期：1998.11.1

  A series of chiral ketones derived from carbohydrates were investigated as catalysts for the asymmetric epoxidation. Fructose-derived ketones are found to be efficient catalysts. The studies show that the structural requirements for the ketone catalysts are very stringent and different types of olefins may require ketones with different structural arrangements. The current study allows us to further understand the chiral ketone catalyzed asymmetric epoxidation and provides some insight for the development of new catalysts.
• Structural probing of d-fructose derived ligands for asymmetric addition of diethylzinc to aldehydes
  作者：Hanmin Huang、Huilin Chen、Xinquan Hu、Changmin Bai、Zhuo Zheng

  DOI：10.1016/s0957-4166(02)00861-3

  日期：2003.2

  A series of new chiral ligands derived from D-fructose have been synthesized and applied in the enantioselective addition of diethylzinc to aldehydes. Comparison of the enantioselectivities obtained with these ligands demonstrated that the catalytic properties are highly dependent upon the structure of ligands, a rational explanation of the structural effects on the catalytic properties is provided. (C) 2003 Elsevier Science Ltd. All rights reserved.