(3aR,6S,6aR)-6-[(S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one | 872326-54-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3aR,6S,6aR)-6-[(S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one
• CAS: 872326-54-0
• 化学式: C₂₂H₃₄O₆Si
• 分子量: 422.594
• InChiKey: MREJJBYZRYRALK-WJFTUGDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3aR,6S,6aR)-6-[(S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以80%的产率得到(3aR,6R,6aR)-6-((S)-2-(benzyloxy)-1-hydroxyethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one
  参考文献：
  名称：

  De Novo Asymmetric Syntheses of d- and l-Talose via an Iterative Dihydroxylation of Dienoates

  摘要：

  A short and highly efficient route to D- and L-talo-gamma-lactones has been developed. The key transformation was the sequential osmium-catalyzed bis-dihydroxylation reaction of substituted 2,4-dienoates. When the first dihydroxylation reaction is performed on (2Z,4E)-dienoates with use of the Sharpless AD-mix procedure, a regio- and enantioselective dihydroxylation resulted along with an in situ lactonization. A subsequent dihydroxylation, using OsO4/NMO in MeOH conditions, resulted in an exceedingly diastereo- and enantioselective synthesis of talo-gamma-lactone.

  DOI：

  10.1021/jo051476+
• 作为产物：
  描述：

  (S)-5-((S)-2'-(benzyloxy)-1'-(tert-butyl(dimethyl)silanyloxy)ethyl)furan-2(5H)-one 在 四氧化锇 、 N-甲基吲哚酮 、 camphor-10-sulfonic acid 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 (3aR,6S,6aR)-6-[(S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one
  参考文献：
  名称：

  De Novo Asymmetric Syntheses of d- and l-Talose via an Iterative Dihydroxylation of Dienoates

  摘要：

  A short and highly efficient route to D- and L-talo-gamma-lactones has been developed. The key transformation was the sequential osmium-catalyzed bis-dihydroxylation reaction of substituted 2,4-dienoates. When the first dihydroxylation reaction is performed on (2Z,4E)-dienoates with use of the Sharpless AD-mix procedure, a regio- and enantioselective dihydroxylation resulted along with an in situ lactonization. A subsequent dihydroxylation, using OsO4/NMO in MeOH conditions, resulted in an exceedingly diastereo- and enantioselective synthesis of talo-gamma-lactone.

  DOI：

  10.1021/jo051476+