(2R,3R,3aR,4R,4aR,5S,8R,8aS,5'S,7E)-2-(5',7'-dimethyl-8'-iodo-7'-octen-1'-yl)-5,10,10-trimethyl-3-[(1,1,1-triphenyl)methoxymethyl]-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole | 214261-07-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2R,3R,3aR,4R,4aR,5S,8R,8aS,5'S,7E)-2-(5',7'-dimethyl-8'-iodo-7'-octen-1'-yl)-5,10,10-trimethyl-3-[(1,1,1-triphenyl)methoxymethyl]-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole
• 英文别名: (1R,2S,5R,6R,7R,9R,10S)-5-[(E,5R)-8-iodo-5,7-dimethyloct-7-enyl]-10,13,13-trimethyl-6-(trityloxymethyl)-4,8-dioxa-3-azatetracyclo[8.2.1.02,9.03,7]tridecane
• CAS: 214261-07-1
• 化学式: C₄₃H₅₄INO₃
• 分子量: 759.811
• InChiKey: MLJFINNAUZGCDE-AZFYEQLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.1
• 重原子数：
  48
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R,3aR,4R,4aR,5S,8R,8aS,5'S,7E)-2-(5',7'-dimethyl-8'-iodo-7'-octen-1'-yl)-5,10,10-trimethyl-3-[(1,1,1-triphenyl)methoxymethyl]-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole 在 盐酸 、 palladium diacetate 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 三乙胺 、 间氯过氧苯甲酸 、 silver carbonate 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 (2R,3R,8R,10E,12E)-3-hydroxy-8,10,12-trimethyl-14-[(2-methylpropan-2-yl)oxy]-14-oxo-2-(trityloxymethyl)tetradeca-10,12-dienoic acid
  参考文献：
  名称：

  Oxazoline N-Oxide-Mediated [2 + 3] Cycloadditions: Application to a Total Synthesis of the Hypocholesterolemic Agent 1233A

  摘要：

  Oxetanone 1233A1 has been synthesized in 22 steps and 3.43% overall yield from 3-methylglutaric anhydride. Asymmetric carbon at C-7 was introduced by a diastereoselective esterification of 3-methylglutaric anhydride, whereas the two asymmetric carbons at C-2' and C-3' were controlled by an asymmetric [2 +/- 3] cycloaddition using camphor-derived oxazoline N-oxide as dipole.

  DOI：

  10.1021/jo980813u
• 作为产物：
  描述：

  (6R,8E)-6,8-dimethyl-9-iodo-8-nonenal 在 4 Angstroem MS 、 二异丁基氢化铝 、 calcium carbonate 作用下， 以 吡啶 、 甲苯 为溶剂， 反应 28.0h， 生成 (2R,3R,3aR,4R,4aR,5S,8R,8aS,5'S,7E)-2-(5',7'-dimethyl-8'-iodo-7'-octen-1'-yl)-5,10,10-trimethyl-3-[(1,1,1-triphenyl)methoxymethyl]-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole
  参考文献：
  名称：

  Oxazoline N-Oxide-Mediated [2 + 3] Cycloadditions: Application to a Total Synthesis of the Hypocholesterolemic Agent 1233A

  摘要：

  Oxetanone 1233A1 has been synthesized in 22 steps and 3.43% overall yield from 3-methylglutaric anhydride. Asymmetric carbon at C-7 was introduced by a diastereoselective esterification of 3-methylglutaric anhydride, whereas the two asymmetric carbons at C-2' and C-3' were controlled by an asymmetric [2 +/- 3] cycloaddition using camphor-derived oxazoline N-oxide as dipole.

  DOI：

  10.1021/jo980813u