1,5-anhydro-2-deoxy-D-threo-hex-1-en-3-ulose | 14125-64-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 1,5-anhydro-2-deoxy-D-threo-hex-1-en-3-ulose
• 英文别名: 1,5-anhydro-2-deoxy-D-threo-hex-1-en-3-ylose；1,5-anhydro-D-threo-hex-1-en-3-ulose；1,5-anhydro-deoxy-D-threo-hex-1-en-3-ulose；(2R,3S)-3-hydroxy-2-(hydroxymethyl)-2,3-dihydropyran-4-one
• CAS: 14125-64-5；26242-05-7；105660-75-1
• 化学式: C₆H₈O₄
• 分子量: 144.127
• InChiKey: DRFLVTOPHKTQAY-PHDIDXHHSA-N

物化性质

• 沸点：
  319.4±37.0 °C(Predicted)
• 密度：
  1.401±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-2-deoxy-D-threo-hex-1-en-3-ulose 、 alkaline earth salt of/the/ methylsulfuric acid 生成 4,6-di-O-acetyl-1,5-anhydro-2-deoxy-D-threo-hex-1-en-3-ulose
  参考文献：
  名称：

  Hydrogen transfer of d-glycals by palladium complexes under ethylene atmosphere

  摘要：

  D-Glucal was oxidized to 1,5-anhydrohex-1-en-3-ulose in, high yield by treatment with a catalytic amount of a palladium complex under ethylene atmosphere. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02556-8
• 作为产物：
  描述：

  D-三乙酰半乳糖烯 在 重铬酸吡啶 、 anion-exchange resin (Amberlite IRN-78, OH^- form) 、 溶剂黄146 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 15.0h， 生成 1,5-anhydro-2-deoxy-D-threo-hex-1-en-3-ulose
  参考文献：
  名称：

  Convenient synthesis of hex-1-enopyran-3-uloses: selective oxidation of allylic alcohols using pyridinium dichromate

  摘要：

  DOI：

  10.1021/jo00376a094

文献信息

• Synthesis of Trisaccharides by Hetero-Diels-Alder Welding of Two Monosaccharide Units
  作者：Jatta A. Himanen、Petri M. Pihko

  DOI：10.1002/ejoc.201200277

  日期：2012.7

  selectivities in the HDA reaction were obtained by using chiral Schiff base chromium complexes. Disaccharide products were accessible by reaction of Danishefsky's diene with acetyl- and benzyl-protected galactoside aldehydes. For the synthesis of trisaccharide products, acetyl-protected glucose or galactose-derived dienes were fused with monosaccharide-derived aldehydes using chromium catalysts for the

  提出了一种基于连接糖单元从头合成的二糖和三糖合成新策略。在该策略中，已经结合糖苷键的功能化单糖构建块使用金属催化的异狄尔斯-阿尔德 (HDA) 反应焊接在一起，以在它们之间生成新的单糖单元。HDA 反应的最高产率和选择性是通过使用手性席夫碱铬配合物获得的。二糖产物可通过DAnishefsky's 二烯与乙酰基和苄基保护的半乳糖苷醛反应获得。为了合成三糖产品，使用铬催化剂将乙酰保护的葡萄糖或半乳糖衍生的二烯与单糖衍生的醛融合以进行 HDA 反应。以中等至良好的收率获得了所需的三糖产品，并具有出色的立体选择性。根据核磁共振光谱和模型研究，在该过程中产生的中心吡喃酮糖环具有 L-顺式-烯酮糖构型。
• Efficient Synthesis of Rare Sugar <scp>d</scp>-Allal via Reversal of Diastereoselection in the Reduction of Protected 1,5-Anhydrohex-1-en-3-uloses: Protecting Group Dependence of the Stereoselection
  作者：Takashi Fujiwara、Masahiko Hayashi

  DOI：10.1021/jo801596q

  日期：2008.11.21

  loses using the NaBH4CeCl3 x 7 H2O system. The crucial point of this synthesis is the nature of the protecting group. When bulky silyl group such as t-butyldiphenylsilyl was used as substrate, protected D-allal was obtained in >99% selectivity. In contrast, when acetylated enone was used, protected D-glucal was obtained exclusively. The addition of CeCl3 x 7 H2O was also found to influence selectivity

  D-alal是通过使用NaBH4 x 7 H2O系统还原大体积的甲硅烷基保护的1，5-脱水己基-1-en-3-uloses选择性获得的。该合成的关键点是保护基团的性质。当使用大体积的甲硅烷基如叔丁基二苯基甲硅烷基作为底物时，以> 99％的选择性获得了受保护的D-alal。相反，当使用乙酰化的烯酮时，仅获得保护的D-葡萄糖。还发现添加CeCl3 x 7 会影响选择性。
• Practical and catalytic synthesis of 1,5-anhydrohex-1-en-3-uloses
  作者：Masahiko Hayashi、Kanako Yamada、Osamu Arikita

  DOI：10.1016/s0040-4020(99)00426-3

  日期：1999.7

  A practical and catalytic method for the preparation of 15-anhydrohex-1-en-3-uloses based on hydrogen transfer of D-glucals by catalytic amount of palladium complex in the presence of olefinic compounds such as ethylene and vinyl acetate has been disclosed. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Dehydrogenation of d-Glycals by Palladium Supported on Activated Charcoal under Ethylene Atmosphere: Synthesis of 1,5-Anhydrohex-1-en-3-uloses
  作者：Masahiko Hayashi

  DOI：10.1055/s-1999-3602

  日期：1999.11
• A facile synthesis of 4,6-O-benzylidene-d-glycals via 1,5-anhydro-4,6-O-benzylidene-d-hex-1-en-3-ulose
  作者：Tohru Sakakibara、Tsubasa Ito、Chika Kotaka、Yasuhiro Kajihara、Yuhya Watanabe、Aki Fujioka

  DOI：10.1016/j.carres.2008.05.018

  日期：2008.11

  Benzylidenation of readily available 1,5-anhydro-D-hex-1-en-3-ulose, followed by sodium borohydride reduction, afforded the title compounds in high yields. Separation of 4,6-O-benzylidene-D-allal and -D-glucal was accomplished by selective acetylation with lipase PS. (C) 2008 Elsevier Ltd. All rights reserved.