(4S-trans)-2-(Hydroxymethyl)-4,5-bis(methoxymethoxy)-2-cyclopenten-1-one | 144811-22-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S-trans)-2-(Hydroxymethyl)-4,5-bis(methoxymethoxy)-2-cyclopenten-1-one
• 英文别名: (4S,5R)-2-(hydroxymethyl)-4,5-bis(methoxymethoxy)cyclopent-2-en-1-one
• CAS: 144811-22-3
• 化学式: C₁₀H₁₆O₆
• 分子量: 232.233
• InChiKey: YCCJYPBYARTNRY-WCBMZHEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S-trans)-2-(Hydroxymethyl)-4,5-bis(methoxymethoxy)-2-cyclopenten-1-one 在 咪唑 、 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 <1R-(1α,4α,5β)>-2-<<(tert-Butyldimethylsilyl)oxy>methyl>-4,5-bis(methoxymethoxy)-2-cyclopenten-1-ol
  参考文献：
  名称：

  Syntheses and absolute configurations of trehazolin and its aglycon

  摘要：

  DOI：

  10.1021/ja00051a051
• 作为产物：
  描述：

  <3aR-(3aα,4α,5β,6α)>-4-(Benzyloxy)-5,6-bis(methoxymethoxy)-3a,4,5,6-tetrahydro-3H-cyclopentisoxazole 在 镍 氢气 、 硼酸 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 5.0h， 以72%的产率得到(4S-trans)-2-(Hydroxymethyl)-4,5-bis(methoxymethoxy)-2-cyclopenten-1-one
  参考文献：
  名称：

  Syntheses of Trehazolin, Trehalamine, and the Aminocyclitol Moiety of Trehazolin: Determination of Absolute Configuration of Trehazolin

  摘要：

  The syntheses and determination of the absolute configurations of trehazolin (1), its aglycon (trehalamine (3)), and its aminocyclitol hexaacetate moiety (5) are described. An important intermediate, optically active epoxide 16 alpha, was obtained from an 11-step synthesis starting from D-glucose. The route has [3+2] cycloaddition and Sharpless epoxidation reactions as the key steps. Trehazolin and trehalamine were subsequently synthesized from 16 alpha, utilizing 2-chloro-3-ethyl-benzoxazolium tetrafluoroborate to construct aminooxazoline frameworks via the carbodiimide derivatives 30 and 27 derived from thioureas 29 and 26, respectively. The absolute configurations of the trehazolin aglycon and aminocyclitol moieties were determined to be [3aR-(3a alpha,4 alpha,5 beta,6 alpha,6a alpha)] and [1R-(1 alpha,2 beta,3 alpha,4 beta,5 beta)], respectively. Alternatively, the synthesis of trehazolin could be completed through nonprotected aminocyclitol 32, which was obtainable from deprotection of compound 5 or degradation of natural trehazolin.

  DOI：

  10.1021/jo00083a023