methyl 2-[(2R,3S,5R,6S)-3-[2-[(2R,4aR,6S,7R,8aS)-7-[tert-butyl(dimethyl)silyl]oxy-2-(4-methoxyphenyl)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]-1-phenylsulfanylethoxy]-5-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]acetate | 917956-39-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-[(2R,3S,5R,6S)-3-[2-[(2R,4aR,6S,7R,8aS)-7-[tert-butyl(dimethyl)silyl]oxy-2-(4-methoxyphenyl)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]-1-phenylsulfanylethoxy]-5-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]acetate
• CAS: 917956-39-9
• 化学式: C₅₁H₆₆O₁₁SSi
• 分子量: 915.23
• InChiKey: CDLLIRVUZSJJBI-NKQUCXIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.07
• 重原子数：
  64
• 可旋转键数：
  21
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl 2-[(2R,3S,5R,6S)-3-[2-[(2R,4aR,6S,7R,8aS)-7-[tert-butyl(dimethyl)silyl]oxy-2-(4-methoxyphenyl)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]-1-phenylsulfanylethoxy]-5-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]acetate 在 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 N,N-二异丙基乙胺 作用下， 以 苯 为溶剂， 反应 1.0h， 以65%的产率得到methyl 2-[(2R,3S,5R,6S)-3-[(E)-2-[(2R,4aR,6S,7R,8aS)-7-[tert-butyl(dimethyl)silyl]oxy-2-(4-methoxyphenyl)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]ethenoxy]-5-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]acetate
  参考文献：
  名称：

  Convergent Assembly of Polycyclic Ethers via Acyl Radical Addition to Unactivated Enol Ether

  摘要：

  [GRAPHICS]A new convergent strategy for assembling 6/6- and 6/7- fused ether ring systems was developed. The key features in our method include Ag+-promoted facile formation of chemically labile enol ether from O,S-acetal and addition of an acyl radical to unactivated enol ether to cyclize a six- or seven-membered ether ring.

  DOI：

  10.1021/ol062349i
• 作为产物：
  描述：

  [(2R,4aR,6S,7R,8aS)-2-(4-methoxyphenyl)-6-(2-phenylsulfanylethyl)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]oxy-tert-butyl-dimethylsilane 在 N-氯代丁二酰亚胺 、 2,6-二叔丁基-4-甲基吡啶 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 methyl 2-[(2R,3S,5R,6S)-3-[2-[(2R,4aR,6S,7R,8aS)-7-[tert-butyl(dimethyl)silyl]oxy-2-(4-methoxyphenyl)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]-1-phenylsulfanylethoxy]-5-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]acetate
  参考文献：
  名称：

  Convergent Assembly of Polycyclic Ethers via Acyl Radical Addition to Unactivated Enol Ether

  摘要：

  [GRAPHICS]A new convergent strategy for assembling 6/6- and 6/7- fused ether ring systems was developed. The key features in our method include Ag+-promoted facile formation of chemically labile enol ether from O,S-acetal and addition of an acyl radical to unactivated enol ether to cyclize a six- or seven-membered ether ring.

  DOI：

  10.1021/ol062349i