Acetic acid (2R,3S,4R,4aR,4bR,8aR,9aS)-3-acetoxy-2-acetoxymethyl-7-iodo-5,5-dimethyl-3,4,4a,4b,5,8,8a,9a-octahydro-2H-benzo[4,5]furo[2,3-b]pyran-4-yl ester | 192439-00-2

• 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: Acetic acid (2R,3S,4R,4aR,4bR,8aR,9aS)-3-acetoxy-2-acetoxymethyl-7-iodo-5,5-dimethyl-3,4,4a,4b,5,8,8a,9a-octahydro-2H-benzo[4,5]furo[2,3-b]pyran-4-yl ester
• 英文别名: [(2R,3S,4R,4aR,4bR,8aR,9aS)-3,4-diacetyloxy-7-iodo-5,5-dimethyl-2,3,4,4a,4b,8,8a,9a-octahydropyrano[2,3-b][1]benzofuran-2-yl]methyl acetate
• CAS: 192439-00-2
• 化学式: C₂₀H₂₇IO₈
• 分子量: 522.334
• InChiKey: PXJOSVXBTFBBQC-NMAPUUFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 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,3S,4R,4aR,4bR,8aR,9aS)-3-acetoxy-2-acetoxymethyl-7-iodo-5,5-dimethyl-3,4,4a,4b,5,8,8a,9a-octahydro-2H-benzo[4,5]furo[2,3-b]pyran-4-yl ester 在 sodium methylate 、 四丁基碘化铵 、 sodium hydride 、 对甲苯磺酸 作用下， 反应 36.5h， 生成 (4aR,4bR,5R,5aS,9aR,10aS,11aR)-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
  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：

  Acetic acid (2R,3R,4S,5S,6S)-3-acetoxy-2-acetoxymethyl-5-iodo-6-[(S)-3-methyl-1-(3-trimethylsilanyl-prop-2-ynyl)-but-2-enyloxy]-tetrahydro-pyran-4-yl ester 在 potassium fluoride 、 18-冠醚-6 、 三乙基硼 、 氧气 、 碘乙烷 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.92h， 生成 Acetic acid (2R,3S,4R,4aR,4bR,8aR,9aS)-3-acetoxy-2-acetoxymethyl-7-iodo-5,5-dimethyl-3,4,4a,4b,5,8,8a,9a-octahydro-2H-benzo[4,5]furo[2,3-b]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