D-苏-五糖,4,5-二脱氧-2,3-O-(1-甲基亚乙基)-(9CI) | 137553-93-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: D-苏-五糖,4,5-二脱氧-2,3-O-(1-甲基亚乙基)-(9CI)
• 英文名称: (4S,5R)-5-ethyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
• CAS: 137553-93-6
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: SQANMADRLWWSPY-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  D-苏-五糖,4,5-二脱氧-2,3-O-(1-甲基亚乙基)-(9CI) 在 palladium dihydroxide 氢气 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.33h， 生成 (4R,5R)-5-ethyl-4-<3-(2,5,5-trimethyl-1,3-dioxan-2-yl)propyl>-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  A transketolase-based synthesis of (+)-exo-brevicomin

  摘要：

  The naturally occurring beetle pheromone (+)-exo-brevicomin was synthesized by a strategy combining chemical and enzymatic steps. The commercially available enzyme transketolase (EC 2.2.1.1) catalyzed the condensation of beta-hydroxypyruvic acid and 2-hydroxybutyraldehyde to furnish the central intermediate in the sequence, optically active hydroxyketone 5. A short sequence converted ketose 5 to protected aldose 8. Wittig extension of the aldehyde followed by hydrogenation and ketal hydrolysis generated the title compound.

  DOI：

  10.1016/s0040-4039(00)93473-7
• 作为产物：
  描述：

  O¹-phosphono-D-threo-5,6-dideoxy-[2]hexulose 在 sodium tetrahydroborate 、 sodium periodate 、 zinc(II) iodide 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 生成 D-苏-五糖,4,5-二脱氧-2,3-O-(1-甲基亚乙基)-(9CI)
  参考文献：
  名称：

  A transketolase-based synthesis of (+)-exo-brevicomin

  摘要：

  The naturally occurring beetle pheromone (+)-exo-brevicomin was synthesized by a strategy combining chemical and enzymatic steps. The commercially available enzyme transketolase (EC 2.2.1.1) catalyzed the condensation of beta-hydroxypyruvic acid and 2-hydroxybutyraldehyde to furnish the central intermediate in the sequence, optically active hydroxyketone 5. A short sequence converted ketose 5 to protected aldose 8. Wittig extension of the aldehyde followed by hydrogenation and ketal hydrolysis generated the title compound.

  DOI：

  10.1016/s0040-4039(00)93473-7

文献信息

• A novel and stereospecific synthesis of (+)-exo-brevicomin
  作者：Sadagopan Raghavan、Suju C. Joseph

  DOI：10.1016/j.tetlet.2003.09.082

  日期：2003.11

  A novel and stereospecific synthesis of (+)-exo-brevicomin is disclosed. The key step of the reaction sequence employs the sulfinyl moiety as an intramolecular nucleophile to functionalize an alkene π-complexed to a bromonium ion.

  公开了（+）-外-brevicomin的新颖的立体定向合成。反应序列的关键步骤是使用亚磺酰基部分作为分子内亲核试剂来官能化与溴离子络合的π烯烃。
• Synthesis of β,γ-disubstituted-γ-lactones through a Johnson–Claisen rearrangement: a short route to xylobovide, nor-canadensolide, canadensolide, sporothriolide and santolinolide
  作者：Rodney A. Fernandes、Arun B. Ingle、Vijay P. Chavan

  DOI：10.1016/j.tetasy.2009.11.018

  日期：2009.12

  The Johnson-Claisen rearrangement of allyl alcohols with chiral vicinal diol functionality was employed to access chiral beta,gamma-disubstituted-gamma-lactones in high enantio- and diastereoselectivity. These were efficiently converted into nor-canadensolide, the advanced gamma-(lactone-lactol) intermediate for xylobovide, canadensolide and sporothriolide and the lactone moiety of the santolinolides. (C) 2009 Elsevier Ltd. All rights reserved.
• A transketolase-based synthesis of (+)-exo-brevicomin
  作者：David C. Myles、Peter J. Andrulis、George M. Whitesides

  DOI：10.1016/s0040-4039(00)93473-7

  日期：1991.9

  The naturally occurring beetle pheromone (+)-exo-brevicomin was synthesized by a strategy combining chemical and enzymatic steps. The commercially available enzyme transketolase (EC 2.2.1.1) catalyzed the condensation of beta-hydroxypyruvic acid and 2-hydroxybutyraldehyde to furnish the central intermediate in the sequence, optically active hydroxyketone 5. A short sequence converted ketose 5 to protected aldose 8. Wittig extension of the aldehyde followed by hydrogenation and ketal hydrolysis generated the title compound.