ethyl 2,3-di-deoxy-D-gluco-oct-2(E)-enoate | 3816-76-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 2,3-di-deoxy-D-gluco-oct-2(E)-enoate
• 英文别名: (E)-ethyl 2,3-dideoxy-D-gluco-oct-2-enoate；trans-2.3-Dehydro-2.3-didesoxy-D-gluco-octansaeure-aethylester；trans-2.3-Dehydro-2.3-didesoxy-D-glycoctansaeure-aethylester；trans-2.3-Dehydro-2.3-didesoxy-D-galacto-octonsaeure-aethylester；ethyl (E,4S,5R,6R,7R)-4,5,6,7,8-pentahydroxyoct-2-enoate
• CAS: 3816-76-0
• 化学式: C₁₀H₁₈O₇
• 分子量: 250.249
• InChiKey: HEWYIJOAFFMJRN-ZCGBZYJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N,O-双(三甲基硅基)氨基甲酸 、 ethyl 2,3-di-deoxy-D-gluco-oct-2(E)-enoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 为溶剂， 反应 24.0h， 生成 (E)-ethyl 2,3-dideoxy-4,5,6,7,8-penta-O-trimethylsilyl-D-gluco-oct-2-enoate
  参考文献：
  名称：

  A straightforward synthesis of glyco-2,7- and 2,8-dienes

  摘要：

  In this paper, we report the efficient preparation of carbohydrate-derived 2,7- and 2,8-dienes. By our synthetic approach, we have quickly converted D-glucose 1 to (E)-ethyl-2,3-dideoxy-D-gluco-oct-2-enoate 5, which led to the desired (E)-ethyl-9,9-dibromo-2,3,8,9-tetradeoxy-4,5,6,7-tetra-(E)-trimethylsilyl-D-gluco-nona-2,8-dienoate 19 with satisfying yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.057
• 作为产物：
  描述：

  4,5,6,7,8-Penta-O-acetyl-2,3-didehydro-2,3-didesoxy-D-gluco-octonsaeure-ethylester 在 氨 作用下， 以 甲醇 为溶剂， 生成 ethyl 2,3-di-deoxy-D-gluco-oct-2(E)-enoate
  参考文献：
  名称：

  Zhdanov,Yu.A. et al., Journal of general chemistry of the USSR, 1965, vol. 35, p. 183 - 185

  摘要：

  DOI：

文献信息

• New route to higher sugars
  作者：N.K. Kochetkov、B.A. Dmitriev

  DOI：10.1016/0040-4020(65)80013-8

  日期：1965.1

  A novel general route to higher aldoses is proposed involving transformation of the starting monosaccharides-2,3-dehydro-2-3-dideoxyaldonic acid or to its ester, by Knoevenage-Doebner condensation or Wittig reaction, folowed by double bond hydroxylation to give higher aldonic acids. The acids are reduced to the corresponding aldoses by conventional methods.

  提出了一种新的制备更高醛糖的一般方法，该方法涉及通过Knoevenage-Doebner缩合或Wittig反应将起始的单糖-2,3-脱氢-2-3-二脱氧醛糖醛酸或其酯转化，然后通过双键羟基化反应得到更高的醛糖。醛糖酸。通过常规方法将酸还原成相应的醛糖。
• Stereochemistry of osmylation of chiral dienes: diastereoselective synthesis of octitols
  作者：Kesavaram Narkunan、Madhavarao Nagarajan

  DOI：10.1039/c39940001705

  日期：——

  The synthesis of higher sugars by hydroxylation of sugar derived dienes 2 and 4 using OsO4–NMO is described.

  描述了使用OsO 4 -NMO通过糖衍生的二烯2和4的羟基化合成高级糖。
• Kochetkov,N.K.; Dmitriev,B.A., Doklady Chemistry, 1963, vol. 151, p. 528 - 531
  作者：Kochetkov,N.K.、Dmitriev,B.A.

  DOI：——

  日期：——
• Zhdanov,Yu.A. et al., Journal of general chemistry of the USSR, 1965, vol. 35, p. 183 - 185
  作者：Zhdanov,Yu.A. et al.

  DOI：——

  日期：——
• A straightforward synthesis of glyco-2,7- and 2,8-dienes
  作者：Franck Dolhem、Nicolas Smiljanic、Catherine Lièvre、Gilles Demailly

  DOI：10.1016/j.tet.2006.05.057

  日期：2006.8

  In this paper, we report the efficient preparation of carbohydrate-derived 2,7- and 2,8-dienes. By our synthetic approach, we have quickly converted D-glucose 1 to (E)-ethyl-2,3-dideoxy-D-gluco-oct-2-enoate 5, which led to the desired (E)-ethyl-9,9-dibromo-2,3,8,9-tetradeoxy-4,5,6,7-tetra-(E)-trimethylsilyl-D-gluco-nona-2,8-dienoate 19 with satisfying yield. (c) 2006 Elsevier Ltd. All rights reserved.