(4aS,4bR,5R,5aS,9aR,10aS,11aS)-2-Iodo-4,4,7,7-tetramethyl-1,4,4a,4b,5,5a,9,9a,10a,11a-decahydro-6,8,10,11-tetraoxa-benzo[b]fluoren-5-ol | 192438-72-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: (4aS,4bR,5R,5aS,9aR,10aS,11aS)-2-Iodo-4,4,7,7-tetramethyl-1,4,4a,4b,5,5a,9,9a,10a,11a-decahydro-6,8,10,11-tetraoxa-benzo[b]fluoren-5-ol
• 英文别名: (1S,3R,8S,9R,10R,11S,16S)-14-iodo-6,6,12,12-tetramethyl-2,5,7,17-tetraoxatetracyclo[8.7.0.03,8.011,16]heptadec-13-en-9-ol
• CAS: 192438-72-5
• 化学式: C₁₇H₂₅IO₅
• 分子量: 436.287
• InChiKey: ADKKKYNGKJYFOY-XSGSKYOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4aS,4bR,5R,5aS,9aR,10aS,11aS)-2-Iodo-4,4,7,7-tetramethyl-1,4,4a,4b,5,5a,9,9a,10a,11a-decahydro-6,8,10,11-tetraoxa-benzo[b]fluoren-5-ol 在 叔丁基锂 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 生成 1-((4aS,4bR,5R,5aS,9aR,10aS,11aS)-5-Benzyloxy-4,4,7,7-tetramethyl-1,4,4a,4b,5,5a,9,9a,10a,11a-decahydro-6,8,10,11-tetraoxa-benzo[b]fluoren-2-yl)-ethanol
  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：

  α-(4'(S),6'-methyl-hept-5'-en-1'-yn-4'-yl)-3,4,6-tri-O-acetyl-2-deoxy-2-iodo-D-mannopyranoside 在 三乙基硼 、 氧气 、 sodium methylate 、 对甲苯磺酸 、 碘乙烷 作用下， 以 正己烷 为溶剂， 反应 18.5h， 生成 (4aS,4bR,5R,5aS,9aR,10aS,11aS)-2-Iodo-4,4,7,7-tetramethyl-1,4,4a,4b,5,5a,9,9a,10a,11a-decahydro-6,8,10,11-tetraoxa-benzo[b]fluoren-5-ol
  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

文献信息

• Polyannulated glycopyranosides via radical-mediated tandem reactions. Stereoselective synthesis of 6·5·6 dioxatricycles via 5-exo-trig, 6-endo-dig mode — III
  作者：H.M.R Hoffmann、U Herden、M Breithor、O Rhode

  DOI：10.1016/s0040-4020(97)00518-8

  日期：1997.6

  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.