(2R,3R)-3-hydroxy-2,4-bis-(tert-butyl-diphenylsilanyloxy)-propionaldehyde | 1360866-39-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2R,3R)-3-hydroxy-2,4-bis-(tert-butyl-diphenylsilanyloxy)-propionaldehyde
• 英文别名: (2R,3R)-2,4-bis[[tert-butyl(diphenyl)silyl]oxy]-3-hydroxybutanal
• CAS: 1360866-39-2
• 化学式: C₃₆H₄₄O₄Si₂
• 分子量: 596.914
• InChiKey: WYHMLWHWNNGAKM-NOCHOARKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-((tert-butyldimethylsilyloxy)methyl)-4,6-dimethoxyphenyl)-2-hydroxyethanone 、 (2R,3R)-3-hydroxy-2,4-bis-(tert-butyl-diphenylsilanyloxy)-propionaldehyde 在 四氯化钛 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 (1S,5'S)-5'-(tert-butyldiphenylsilyloxy)-6'-((tert-butyldiphenylsilyloxy)methyl)-5,7-dimethoxy-3',4',5',6'-tetrahydro-3H-spiro-[isobenzofuran-1,2'-pyran]-3',4'-diol 、 (1S,5'S)-5'-(tert-butyldiphenylsilyloxy)-6'-((tert-butyldiphenylsilyloxy)methyl)-5,7-dimethoxy-3',4',5',6'-tetrahydro-3H-spiro-[isobenzofuran-1,2'-pyran]-3',4'-diol
  参考文献：
  名称：

  Synthesis of O-Spiro-C-Aryl Glycosides Using Organocatalysis

  摘要：

  An organocatalysis strategy has been developed toward the synthesis of O-spiro-C-aryl glycosides with different configurations in the sugar part. This strategy has been extended to the synthesis of the Papulacandin class of compounds.

  DOI：

  10.1021/jo202353r
• 作为产物：
  描述：

  (tert-butyldiphenylsilanyloxy)acetaldehyde 在 D-脯氨酸 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以70%的产率得到(2R,3R)-3-hydroxy-2,4-bis-(tert-butyl-diphenylsilanyloxy)-propionaldehyde
  参考文献：
  名称：

  Synthesis of O-Spiro-C-Aryl Glycosides Using Organocatalysis

  摘要：

  An organocatalysis strategy has been developed toward the synthesis of O-spiro-C-aryl glycosides with different configurations in the sugar part. This strategy has been extended to the synthesis of the Papulacandin class of compounds.

  DOI：

  10.1021/jo202353r

文献信息

• Synthesis of <i>O</i>-Spiro-<i>C</i>-Aryl Glycosides Using Organocatalysis
  作者：Prathama S. Mainkar、Kancharla Johny、Tadikamalla Prabhakar Rao、Srivari Chandrasekhar

  DOI：10.1021/jo202353r

  日期：2012.3.2

  An organocatalysis strategy has been developed toward the synthesis of O-spiro-C-aryl glycosides with different configurations in the sugar part. This strategy has been extended to the synthesis of the Papulacandin class of compounds.