tert-butyl(((4R,5S)-5-((R)-1-(tert-butyldimethylsilyloxy)-2-methylallyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)dimethylsilane | 1448243-35-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl(((4R,5S)-5-((R)-1-(tert-butyldimethylsilyloxy)-2-methylallyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)dimethylsilane
• CAS: 1448243-35-3
• 化学式: C₂₂H₄₆O₄Si₂
• 分子量: 430.776
• InChiKey: CRPGQQVGNPIQIR-QRVBRYPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.49
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl(((4R,5S)-5-((R)-1-(tert-butyldimethylsilyloxy)-2-methylallyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)dimethylsilane 在 camphor-10-sulfonic acid 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 以90%的产率得到((4R,5S)-5-((R)-1-(tert-butyldimethylsilyloxy)-2-methylallyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol
  参考文献：
  名称：

  A C2-Symmetric Pool Based Synthesis of the Furanoside of Hygromycin A

  摘要：

  The readily available and inexpensive D-tartaric acid serves as the chiral building block for synthesis of the furanoside of hygromycin A. Key to our successes in the asymmetric synthesis of the furanose segment was the melding of several key reactions, such as the successful application of the monosilylation of C-2-symmetric diol, diastereocontrolled di(2-propenyl)zinc addition to the aldehyde, and TMSCl-MeOH promoted desilylation, acetal-cleavage, and intramolecular esterification in one-step.

  DOI：

  10.3987/com-12-s(n)19
• 作为产物：
  描述：

  (4S,5S)-2,2-1,3-二氧戊环-4,5-二羧酸二甲酯 在 sodium tetrahydroborate 、 三氧化硫吡啶 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 22.49h， 生成 tert-butyl(((4R,5S)-5-((R)-1-(tert-butyldimethylsilyloxy)-2-methylallyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)dimethylsilane
  参考文献：
  名称：

  A C2-Symmetric Pool Based Synthesis of the Furanoside of Hygromycin A

  摘要：

  The readily available and inexpensive D-tartaric acid serves as the chiral building block for synthesis of the furanoside of hygromycin A. Key to our successes in the asymmetric synthesis of the furanose segment was the melding of several key reactions, such as the successful application of the monosilylation of C-2-symmetric diol, diastereocontrolled di(2-propenyl)zinc addition to the aldehyde, and TMSCl-MeOH promoted desilylation, acetal-cleavage, and intramolecular esterification in one-step.

  DOI：

  10.3987/com-12-s(n)19