α-(4'(S),6'-methyl-hept-5'-en-1'-yn-4'-yl)-3,4,6-tri-O-acetyl-2-deoxy-2-iodo-D-mannopyranoside | 192438-83-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-(4'(S),6'-methyl-hept-5'-en-1'-yn-4'-yl)-3,4,6-tri-O-acetyl-2-deoxy-2-iodo-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6S)-3,4-diacetyloxy-5-iodo-6-[(4S)-6-methylhept-5-en-1-yn-4-yl]oxyoxan-2-yl]methyl acetate
• CAS: 192438-83-8
• 化学式: C₂₀H₂₇IO₈
• 分子量: 522.334
• InChiKey: ZCBKXFBWWRAKIY-HUTLCRKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  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 、 水 、 叔丁基锂 、 氧气 、 sodium methylate 、 四丁基碘化铵 、 sodium hydride 、 对甲苯磺酸 、 碘乙烷 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 39.5h， 生成 (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：

  乙酰化葡萄烯糖 在 N-碘代丁二酰亚胺 、 四丁基氟化铵 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 50.0h， 生成 α-(4'(S),6'-methyl-hept-5'-en-1'-yn-4'-yl)-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