(3aS,5S,5aR,8aR,8bS)-2,2,5,7,7-五甲基四氢-3aH-二[1,3]二氧杂环戊并[4,5-b:4',5'-d]吡喃 | 136572-16-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 中文名称: (3aS,5S,5aR,8aR,8bS)-2,2,5,7,7-五甲基四氢-3aH-二[1,3]二氧杂环戊并[4,5-b:4',5'-d]吡喃
• 英文名称: 1,2:3,4-di-O-isopropylidene-L-fucopyranose
• 英文别名: 1,2:3,4-di-O-isopropylidene-α-L-fucose；O¹,O²;O³,O⁴-diisopropylidene-α-L-fucopyranose；O¹,O²;O³,O⁴-Diisopropyliden-α-L-fucopyranose；1,2,3,4-DI-O-ISOPROPYLIDENE-alpha-L-FUCOPYRANOSIDE；(1R,2S,6S,8S,9R)-4,4,8,11,11-pentamethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
• CAS: 136572-16-2
• 化学式: C₁₂H₂₀O₅
• 分子量: 244.288
• InChiKey: FBWQLTARTKWGMT-MBXMOIHESA-N

物化性质

• 沸点：
  285.7±35.0 °C(Predicted)
• 密度：
  1.076±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  L(-)岩藻糖 在 硫酸 、 丙酮 作用下， 生成 (3aS,5S,5aR,8aR,8bS)-2,2,5,7,7-五甲基四氢-3aH-二[1,3]二氧杂环戊并[4,5-b:4',5'-d]吡喃
  参考文献：
  名称：

  277.将d-果糖从其他天然糖中分离出来，即其2：3-4：5-双丙酮和1：2-单丙酮衍生物：单糖的丙酮衍生物对冷的癸酸硫酸行为的观察

  摘要：

  DOI：

  10.1039/jr9470001461

文献信息

• Tandem Acetalation−Acetylation of Sugars and Related Derivatives with Enolacetates under Solvent-Free Conditions
  作者：Debaraj Mukherjee、Bhahwal Ali Shah、Pankaj Gupta、Subhash Chandra Taneja

  DOI：10.1021/jo070363i

  日期：2007.11.1

  [GRAPHICS]Molecular iodine catalyzes acetalation and acetylation of reducing sugars and sugar glycosides with stoichiometric amounts of enol acetates under solvent-free conditions, thereby facilitating the synthesis of various types of orthogonally protected sugar derivatives in short time and good yields. The outcome of the reaction can be controlled by variation in temperature. Thus at lower temperature, it is possible to obtain the acetonide acetate as a single product whereas peracetate is the major product at higher temperature.
• Nano<i>n</i>-Propylsulfonated Magnetic γ-Fe₂O₃as an Efficient and Reusable Catalyst for the Synthesis<i>O</i>-Isopropylidene Derivatives of Carbohydrates
  作者：Xiaoran Zhang、Changqiang Zhang

  DOI：10.1080/07328303.2013.804082

  日期：2013.5.4

  Nano n-propylsulfonated -Fe2O3 was found to be a highly efficient, reusable heterogeneous catalyst for the conversion of a range of monosaccharides and some of their derivatives to the corresponding O-isopropylidene derivatives in good to excellent yields by refluxing the reaction mixture in dry acetone. The magnetic property of the catalyst enabled its separation from the reaction mixture by a simple process of filtration along with the aid of an external magnet. The efficiency of the catalyst was found to be largely unaffected for at least up to six cycles of reuse, thus proving the new methodology to be environmentally rewarding besides being simple and facile in operation.
• O-Isopropylidenation of carbohydrates catalyzed by vanadyl triflate
  作者：Chun-Cheng Lin、Mi-Dan Jan、Shiue-Shien Weng、Chang-Ching Lin、Chien-Tien Chen

  DOI：10.1016/j.carres.2006.04.001

  日期：2006.8

  Vanadyl triflate has been identified as a mild and efficient catalyst for the chemoselective O-isopropylidenation of functionalized carbohydrates with acetone and acetone equivalents. The current protocol is compatible with a diverse array of protecting groups and the products can be readily isolated by simple aqueous wash. (c) 2006 Elsevier Ltd. All rights reserved.
• Freudenberg; Raschig, Chemische Berichte, 1927, vol. 60, p. 1633
  作者：Freudenberg、Raschig

  DOI：——

  日期：——
• 277. The separation of d-fructose from other natural sugars as its 2 : 3–4 : 5-diacetone and 1 : 2-monoacetone derivatives : observations on the behaviour of acetoné derivatives of monosaccharides towards cold decinormal sulphuric acid
  作者：D. J. Bell

  DOI：10.1039/jr9470001461

  日期：——