1-O-menthyloxycarbonylmyo-inositol | 139686-86-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-O-menthyloxycarbonylmyo-inositol
• 英文别名: 3-O-menthoxycarbonyl myo-inositol
• CAS: 139686-86-5
• 化学式: C₁₇H₃₀O₈
• 分子量: 362.42
• InChiKey: LTKAJZRCIMCHPD-OBFRQOQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.21
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  136.68
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  Inositol 在 碳酸氢钠 、 对甲苯磺酸 、 三丁基氧化锡 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 生成 1-O-menthyloxycarbonylmyo-inositol
  参考文献：
  名称：

  Synthesis of D-erythro-sphingomyelin and of D-erythro-ceramide-1-phosphoinositol

  摘要：

  3-0-Silyl-protected azidosphingosine 3, readily available from D-erythro-azidosphingosine, is transformed into ceramidyl phosphite derivative 5 which is a versatile building block for the synthesis of ceramide-1-0-phosphate and derivatives. This is exhibited for the synthesis of the title compounds 1 and 2.

  DOI：

  10.1016/s0040-4039(00)91820-3

文献信息

• The regioselective synthesis of enantiomerically pure myo-inositol derivatives. Efficient synthesis of myo-inositol 1,4,5-trisphosphate.
  作者：Agustín Aguiló、Manuel Martín-Lomas、Soledad Penadés

  DOI：10.1016/s0040-4039(00)74142-6

  日期：1992.1

  tonate and then acylation with (−)-menthyl chloroformate. Diastereomerically pure 1-O-(−)-menthoxycarbonyl-myo-inositol 1 can be used as starting material for the preparation of biologically important myo-inositol phosphates and glycosyl phosphatidylinositols in a shorter and effective way.

  肌醇的区域选择性1- O-酰化和同时的光学拆分已通过渗碳，使用二正丁基锡-双-乙酰丙酮酸的金属转移，然后再与（-）-薄荷基氯甲酸酯酰化来实现。非对映体纯的1- ø - （ - ） - menthoxycarbonyl-肌醇肌醇1可以用作用于制备生物学上重要的起始材料肌肉在更短的和有效的方式肌醇磷酸盐和糖基磷脂酰肌醇。
• Regioselective functionalization of unprotected myo-inositol by electrophilic substitution
  作者：Yutaka Watanabe、Tsuyoshi Uemura、Satoe Yamauchi、Kousei Tomita、Takafumi Saeki、Ryousuke Ishida、Minoru Hayashi

  DOI：10.1016/j.tet.2013.03.109

  日期：2013.6

  Unprotected myo-inositol was treated with various electrophiles, such as aroyl chlorides, tosyl chloride and tert-butyldiphenylsilyl chloride in a solution of LiCl/DMA or DMSO to afford regioselectively l,3-di-O-substituted or racemic 1-O-substituted derivatives, depending on a quantity of reagents and reaction time. alpha-Unbranched alkanoic acid anhydrides in LiCl/DMA in the presence of triethylamine were suitable for acylation of myo-inositol, in contrast to the fact that acylation using alkanoyl chlorides in aprotic polar solvents generally does not proceed well due to decomposition of the reagents by the reaction with the solvents. (C) 2013 Elsevier Ltd. All rights reserved.