methyl 3(S)-3-<1(S)-4-((tert-butyldiphenylsilyl)oxy)-1-(hydroxymethyl)butoxy>-3-<4(R)-2,2-dimethyl-<1,3>dioxolan-4-yl>propionate | 219916-40-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3(S)-3-<1(S)-4-((tert-butyldiphenylsilyl)oxy)-1-(hydroxymethyl)butoxy>-3-<4(R)-2,2-dimethyl-<1,3>dioxolan-4-yl>propionate
• 英文别名: methyl (3S)-3-[(2S)-5-[tert-butyl(diphenyl)silyl]oxy-1-hydroxypentan-2-yl]oxy-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate
• CAS: 219916-40-2
• 化学式: C₃₀H₄₄O₇Si
• 分子量: 544.761
• InChiKey: MMVVLDYHCBKBBS-MSLLRLGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3(S)-3-<1(S)-4-((tert-butyldiphenylsilyl)oxy)-1-(hydroxymethyl)butoxy>-3-<4(R)-2,2-dimethyl-<1,3>dioxolan-4-yl>propionate 在 palladium on activated charcoal 咪唑 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 草酰氯 、 TEA 、 camphor-10-sulfonic acid 、 氢气 、 sodium hydride 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 21.0h， 生成 ethyl 4(S)-7-((tert-butyldiphenylsilyl)oxy)-4-<1(S)-1-(4(R)-2,2-dimethyl<1,3>dioxolan-4-yl)propoxy>heptanoate
  参考文献：
  名称：

  Enantioselective Synthesis of α,β,α‘-Trisubstituted Cyclic Ethers

  摘要：

  A synthetic strategy for the preparation of trisusbstituted cyclic ethers is presented, in which the stereochemistry at the carbon atoms adjacent to the oxygen of the ether was controlled by means of a hetero Diels-Alder reaction between a monoactivated diene and a chiral aldehyde. The adducts were transformed into linear ethers, which were then used for the preparation of cis and trans cyclic ethers of different sizes. A cis-oxepane, cis-oxonane, and cis-oxocane and a trans-oxocane were prepared as examples of the scope of the strategy.

  DOI：

  10.1021/jo981188w
• 作为产物：
  描述：

  (S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,6-dihydro-2H-pyran 在 sodium tetrahydroborate 、 臭氧 作用下， 以 乙醚 为溶剂， 反应 18.0h， 生成 methyl 3(S)-3-<1(S)-4-((tert-butyldiphenylsilyl)oxy)-1-(hydroxymethyl)butoxy>-3-<4(R)-2,2-dimethyl-<1,3>dioxolan-4-yl>propionate
  参考文献：
  名称：

  Enantioselective Synthesis of α,β,α‘-Trisubstituted Cyclic Ethers

  摘要：

  A synthetic strategy for the preparation of trisusbstituted cyclic ethers is presented, in which the stereochemistry at the carbon atoms adjacent to the oxygen of the ether was controlled by means of a hetero Diels-Alder reaction between a monoactivated diene and a chiral aldehyde. The adducts were transformed into linear ethers, which were then used for the preparation of cis and trans cyclic ethers of different sizes. A cis-oxepane, cis-oxonane, and cis-oxocane and a trans-oxocane were prepared as examples of the scope of the strategy.

  DOI：

  10.1021/jo981188w