(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]fluorene | 192439-23-9

• 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)-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]fluorene
• 英文别名: (1S,3R,8S,9R,10R,11S,16S)-6,6,12,12-tetramethyl-9-phenylmethoxy-2,5,7,17-tetraoxatetracyclo[8.7.0.03,8.011,16]heptadec-13-ene
• CAS: 192439-23-9
• 化学式: C₂₄H₃₂O₅
• 分子量: 400.515
• InChiKey: DTCUESIXKBXTFB-CKBSPGBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (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]fluorene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以30%的产率得到(1R,2S,8S,10S,12R,17S,18R)-3,3,15,15-tetramethyl-18-phenylmethoxy-5,9,11,14,16-pentaoxapentacyclo[8.8.0.02,8.04,6.012,17]octadecane
  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：

  (4aS,4bR,5R,5aS,9aR,10aS,11aS)-5-Benzyloxy-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]fluorene 在 水 、 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 以59%的产率得到(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]fluorene
  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.