R,R-3,4-dibenzyloxy-threo-hexa-1,5-diene | 111555-72-7

• 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: R,R-3,4-dibenzyloxy-threo-hexa-1,5-diene
• 英文别名: (3R,4R)-3,4-Di-O-benzyl-1,5-hexadiene-3,4-diol；[(3R,4R)-4-phenylmethoxyhexa-1,5-dien-3-yl]oxymethylbenzene
• CAS: 111555-72-7
• 化学式: C₂₀H₂₂O₂
• 分子量: 294.393
• InChiKey: SIDNFRGHUJGCFX-WOJBJXKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  R,R-3,4-dibenzyloxy-threo-hexa-1,5-diene 在 palladium on activated charcoal 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium chlorite 、 四氧化锇 、 十二/十四烷基二甲基氧化胺 、 camphor-10-sulfonic acid 、 氢气 、 silver(l) oxide 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 生成 D-chitaric acid
  参考文献：
  名称：

  使用催化四氧化对1,5-二烯进行一般的氧化环化反应。

  摘要：

  DOI：

  10.1002/anie.200390253
• 作为产物：
  描述：

  3,4-dibenzyloxy-1,2,5,6-tetra-O-mesyl-D-mannitol 在 sodium iodide 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以45%的产率得到R,R-3,4-dibenzyloxy-threo-hexa-1,5-diene
  参考文献：
  名称：

  Gurjar, M. K.; Pawar, S. M., Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1987, vol. 26, p. 55 - 56

  摘要：

  DOI：

文献信息

• Applications of Cyclic Sulfates of <i>vic</i>-Diols:  Synthesis of Episulfides, Olefins, and Thio Sugars
  作者：Francisco G. Calvo-Flores、Pilar García-Mendoza、Fernando Hernández-Mateo、Joaquín Isac-García、Francisco Santoyo-González

  DOI：10.1021/jo962066b

  日期：1997.6.13

  A new efficient and expeditious one-pot synthesis of thiiranes and olefins from cyclic sulfates of vic-diols is described. Opening of cyclic sulfates with potassium thioacetate or potassium thiocyanate followed by treatment with sodium methoxide led to episulfides. Olefins were obtained when potassium selenocyanate was used as nucleophile, and the obtained monoesters were treated with sodium borohydride. This method was applied to acyclic polyols derived from chiral glycerine, 1,2-isopropylidenehexofuranoses with different subtituents at C-3, and dimethyl acetals derived from pentoses and hexoses. The methodology is highly versatile, and its applicability has been demonstrated by the synthesis of different 4- and 5-thiosugars by opening of the thiirane ring with sodium acetate or lithium aluminum hydride. Reduction with lithium aluminum hydride of the thiocyanate sulfate potassium salt obtained by the opening of cyclic sulfate with KSCN allowed the direct synthesis of 5-deoxy-4-thio- and 6-deoxy-5-thiosugars. Cyclic thiosugars with the sulfur atom in the ring are obtained by acidic hydrolysis of the 5-thiol derivatives of 1,2-O-isopropylidenehexofuranoses and 4-thiopentose dimethyl acetals. Using this method, an efficient synthesis of 5-thio-L-fucose as well as the synthesis of 2,5-dideoxy-4-thiofuranose is described.
• GURJAR, M. K.;PAWAR, S. M., INDIAN J. CHEM., 26,(1987) N 1, 55-56
  作者：GURJAR, M. K.、PAWAR, S. M.

  DOI：——

  日期：——
• A General Oxidative Cyclization of 1,5-Dienes Using Catalytic Osmium Tetroxide
  作者：Timothy J. Donohoe、Sam Butterworth

  DOI：10.1002/anie.200390253

  日期：2003.2.24
• Gurjar, M. K.; Pawar, S. M., Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1987, vol. 26, p. 55 - 56
  作者：Gurjar, M. K.、Pawar, S. M.

  DOI：——

  日期：——