Acetic acid (2R,3R,4S,5S,6S)-3-acetoxy-2-acetoxymethyl-6-((R)-1-cyclohexylidenemethyl-but-3-ynyloxy)-5-iodo-tetrahydro-pyran-4-yl ester | 192438-88-3

• 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-((R)-1-cyclohexylidenemethyl-but-3-ynyloxy)-5-iodo-tetrahydro-pyran-4-yl ester
• CAS: 192438-88-3
• 化学式: C₂₃H₃₁IO₈
• 分子量: 562.399
• InChiKey: YXWDSZSPDUJFQV-ZGRTYHRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5S,6S)-3-acetoxy-2-acetoxymethyl-6-((R)-1-cyclohexylidenemethyl-but-3-ynyloxy)-5-iodo-tetrahydro-pyran-4-yl ester 在 三乙基硼 、 氧气 、 碘乙烷 作用下， 以 正己烷 为溶剂， 反应 0.33h， 以44%的产率得到2(R),3(S),4(R),4a(R),4b(R),8a(R),9a(S)-2-acetoxymethyl-5,5-cyclohexylen-7-iodo-3,4,4a,4b,5,8,8a,9a-octahydro-2H-pyrano[2,3-b]benzofuran-3,4-diol diacetate
  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：

  乙酰化葡萄烯糖 在 potassium fluoride 、 N-碘代丁二酰亚胺 、 18-冠醚-6 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 168.0h， 生成 Acetic acid (2R,3R,4S,5S,6S)-3-acetoxy-2-acetoxymethyl-6-((R)-1-cyclohexylidenemethyl-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