ethyl 3-((4R,5R)-5-formyl-2,2-dimethyl-1,3-dioxolan-4-yl)propanoate | 95517-36-5

• 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 3-((4R,5R)-5-formyl-2,2-dimethyl-1,3-dioxolan-4-yl)propanoate
• 英文别名: ethyl (4R,5R)-5-formyl-4,5-isopropylidenedioxypentanoate；ethyl 3-[(4R,5R)-5-formyl-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate
• CAS: 95517-36-5；124575-40-2；140836-87-9
• 化学式: C₁₁H₁₈O₅
• 分子量: 230.261
• InChiKey: BKTHURYZNPBODJ-BDAKNGLRSA-N

物化性质

• 沸点：
  294.3±25.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-((4R,5R)-5-formyl-2,2-dimethyl-1,3-dioxolan-4-yl)propanoate 在 盐酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 生成 sapinofuranone A
  参考文献：
  名称：

  Total synthesis of sapinofuranone A from d-ribose

  摘要：

  The total synthesis of sapinofuranone A has been achieved starting from naturally occurring carbohydrate D-ribose via a short and high yielding route. The key transformations include Wittig olefination, Ohira-Bestmann reaction, Sonogashira coupling. Finally acetonide deprotection and subsequent lactonization using catalytic amount of hydrochloric acid completed the total synthesis of sapinofuranone A. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.012
• 作为产物：
  描述：

  2,3-异亚丙氧基-D-呋喃核糖苷 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 、 苯甲酸 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 36.0h， 生成 ethyl 3-((4R,5R)-5-formyl-2,2-dimethyl-1,3-dioxolan-4-yl)propanoate
  参考文献：
  名称：

  Total synthesis of sapinofuranone A from d-ribose

  摘要：

  The total synthesis of sapinofuranone A has been achieved starting from naturally occurring carbohydrate D-ribose via a short and high yielding route. The key transformations include Wittig olefination, Ohira-Bestmann reaction, Sonogashira coupling. Finally acetonide deprotection and subsequent lactonization using catalytic amount of hydrochloric acid completed the total synthesis of sapinofuranone A. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.012

文献信息

• An acyl radical initiated tandem 7-endo/5-exo radical cyclization approach to enantiomerically pure bicyclo[5.3.0]decan-2-ones
  作者：Duncan Batty、David Crich

  DOI：10.1016/s0040-4039(00)91564-8

  日期：1992.2

  oic acids from the chiral pool is described. The phenylseleno esters derived from these acids undergo cyclization with tributyltin hydride to give mixtures of cyclohexanones and cycloheptanones. The inclusion of the appropriate four carbon side chain at C-7 leads, via a tandem radical cyclization process, to the title compounds in moderate yield.

  描述了从手性池制备赤型和苏型4，5-二羟基庚基6-烯酸的丙酮化物衍生物。衍生自这些酸的苯基硒烯酸酯与氢化三丁基锡进行环化，得到环己酮和环庚酮的混合物。通过串联自由基环化过程，在C-7处包含适当的四个碳侧链，从而以中等收率得到标题化合物。
• Batty, Duncan; Crich, David, Journal of the Chemical Society. Perkin transactions I, 1992, # 23, p. 3193 - 3204
  作者：Batty, Duncan、Crich, David

  DOI：——

  日期：——
• Betty Duncan, Crich David, J. Chem. Soc. Perkin Trans. 1, (1992) N 23, S 3193- 3204
  作者：Betty Duncan, Crich David

  DOI：——

  日期：——
• Total synthesis of sapinofuranone A from d-ribose
  作者：Lingaiah Nagarapu、Shuklachary Karnakanti、Rajashaker Bantu

  DOI：10.1016/j.tet.2012.05.012

  日期：2012.7

  The total synthesis of sapinofuranone A has been achieved starting from naturally occurring carbohydrate D-ribose via a short and high yielding route. The key transformations include Wittig olefination, Ohira-Bestmann reaction, Sonogashira coupling. Finally acetonide deprotection and subsequent lactonization using catalytic amount of hydrochloric acid completed the total synthesis of sapinofuranone A. (C) 2012 Elsevier Ltd. All rights reserved.