<1S-(1α,4β,5α)>-2-<<(tert-Butyldimethylsilyl)oxy>methyl>-4,5-bis(methoxymethoxy)-2-cyclopenten-1-ol | 144901-13-3

• 英文名称: <1S-(1α,4β,5α)>-2-<<(tert-Butyldimethylsilyl)oxy>methyl>-4,5-bis(methoxymethoxy)-2-cyclopenten-1-ol
• 英文别名: (1S,4S,5S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4,5-bis(methoxymethoxy)cyclopent-2-en-1-ol
• CAS: 144901-13-3
• 化学式: C₁₆H₃₂O₆Si
• 分子量: 348.512
• InChiKey: YPXTYBHTMJTGPF-SOUVJXGZSA-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：

  <1S-(1α,4β,5α)>-2-<<(tert-Butyldimethylsilyl)oxy>methyl>-4,5-bis(methoxymethoxy)-2-cyclopenten-1-ol 在 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 <3S-(3α,4β,5β)>-5-Benzyloxy-1-hydroxymethyl-3,4-di(methoxymethoxy)-1-cyclopentene
  参考文献：
  名称：

  Synthesis of 5-epi-trehazolin (trehalostatin).

  摘要：

  5-表-trehazolin（trehalostatin）（2）的合成是通过从D-葡萄糖中提取的关键中间体环氧化物（6α）完成的。通过比较相关质子的核磁共振弛豫时间，确定了从Sharpless环氧化反应中获得的环氧化物（6α）及其异构体（6β）的立体化学。

  DOI：

  10.7164/antibiotics.47.932
• 作为产物：
  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 25.67h， 生成 <1S-(1α,4β,5α)>-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