Acetic acid (2R,3R,4S,5S,6S)-3-acetoxy-2-acetoxymethyl-6-((S)-1-cyclopent-1-enyl-4-trimethylsilanyl-but-3-ynyloxy)-5-iodo-tetrahydro-pyran-4-yl ester | 192438-89-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (2R,3R,4S,5S,6S)-3-acetoxy-2-acetoxymethyl-6-((S)-1-cyclopent-1-enyl-4-trimethylsilanyl-but-3-ynyloxy)-5-iodo-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3R,4S,5S,6S)-3,4-diacetyloxy-6-[(1S)-1-(cyclopenten-1-yl)-4-trimethylsilylbut-3-ynoxy]-5-iodooxan-2-yl]methyl acetate
• CAS: 192438-89-4
• 化学式: C₂₄H₃₅IO₈Si
• 分子量: 606.527
• InChiKey: JFJWUHJKWWEMOG-FZPZUOBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5S,6S)-3-acetoxy-2-acetoxymethyl-6-((S)-1-cyclopent-1-enyl-4-trimethylsilanyl-but-3-ynyloxy)-5-iodo-tetrahydro-pyran-4-yl ester 在 potassium fluoride 、 18-冠醚-6 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.42h， 以86%的产率得到α-(4'(S)-cyclopent-5'-enyl-but-1'-ynyl)-3,4,6-tri-O-acetyl-2-deoxy-2-iodo-D-mannopyranoside
  参考文献：
  名称：

  Polyannulated glycopyranosides via radical-mediated tandem reactions. Stereoselective synthesis of 6·5·6 dioxatricycles via 5-exo-trig, 6-endo-dig mode — III

  摘要：

  A series of C-silylated enynols, e.g. 6-methyl-1-trimethylsilyl-hept-5-en-1-yn-4-ol (rac-A) was prepared and submitted to N-iodosuccinimide mediated iodoalkoxylation of tri-O-acetylglycal. Thanks to the presence of the silyl group the resulting diastereomeric glycosides (S)A(1) and (R)A(1) were readily separated. Triethylborane/oxygen/ethyl iodide promoted iodine transfer afforded doubly annulated glycosides in a 5-eso-trigonal, 6-endo-digonal cascade. The required re-protection of the three acetoxy groups was carried out orthogonally The newly installed iodocyclohexene moiety served as site for further functionalization, which was accomplished by metal-halogen exchange followed by electrophilic capture or by reduction/epoxidation. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00518-8
• 作为产物：
  描述：

  1-Cyclopent-1-enyl-4-trimethylsilanyl-but-3-yn-1-ol 、 乙酰化葡萄烯糖 在 N-碘代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以24%的产率得到Acetic acid (2R,3R,4S,5S,6S)-3-acetoxy-2-acetoxymethyl-6-((S)-1-cyclopent-1-enyl-4-trimethylsilanyl-but-3-ynyloxy)-5-iodo-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Polyannulated glycopyranosides via radical-mediated tandem reactions. Stereoselective synthesis of 6·5·6 dioxatricycles via 5-exo-trig, 6-endo-dig mode — III

  摘要：

  A series of C-silylated enynols, e.g. 6-methyl-1-trimethylsilyl-hept-5-en-1-yn-4-ol (rac-A) was prepared and submitted to N-iodosuccinimide mediated iodoalkoxylation of tri-O-acetylglycal. Thanks to the presence of the silyl group the resulting diastereomeric glycosides (S)A(1) and (R)A(1) were readily separated. Triethylborane/oxygen/ethyl iodide promoted iodine transfer afforded doubly annulated glycosides in a 5-eso-trigonal, 6-endo-digonal cascade. The required re-protection of the three acetoxy groups was carried out orthogonally The newly installed iodocyclohexene moiety served as site for further functionalization, which was accomplished by metal-halogen exchange followed by electrophilic capture or by reduction/epoxidation. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00518-8