<1R-(1α,4α,5β)>-2-<<(tert-Butyldimethylsilyl)oxy>methyl>-4,5-bis(methoxymethoxy)-2-cyclopenten-1-ol | 144811-24-5

• 英文名称: <1R-(1α,4α,5β)>-2-<<(tert-Butyldimethylsilyl)oxy>methyl>-4,5-bis(methoxymethoxy)-2-cyclopenten-1-ol
• 英文别名: (1R,4S,5S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4,5-bis(methoxymethoxy)cyclopent-2-en-1-ol
• CAS: 144811-24-5
• 化学式: C₁₆H₃₂O₆Si
• 分子量: 348.512
• InChiKey: YPXTYBHTMJTGPF-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  <1R-(1α,4α,5β)>-2-<<(tert-Butyldimethylsilyl)oxy>methyl>-4,5-bis(methoxymethoxy)-2-cyclopenten-1-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 四丁基氟化铵 、 sodium hydride 、 D-(-)-酒石酸二异丙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 9.0h， 生成 <1S-(1α,2β,3α,4β,5α)>-2-(Benzyloxy)-1-(hydroxymethyl)-3,4-bis(methoxymethoxy)-6-oxabicyclo<3.1.0>hexane
  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
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 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 25.67h， 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 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

文献信息

• Syntheses and absolute configurations of trehazolin and its aglycon
  作者：Yoshiyuki Kobayashi、Hideki Miyazaki、Masao Shiozaki

  DOI：10.1021/ja00051a051

  日期：1992.12