(E)-(2S,4S,8S,10R,11S)-1-{(4R,6R)-6-[(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-4-hydroxy-13-iodo-2,8-bis-(4-methoxy-benzyloxy)-11-methyl-10-triisopropylsilanyloxy-tridec-12-en-6-one | 332179-92-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-(2S,4S,8S,10R,11S)-1-{(4R,6R)-6-[(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-4-hydroxy-13-iodo-2,8-bis-(4-methoxy-benzyloxy)-11-methyl-10-triisopropylsilanyloxy-tridec-12-en-6-one
• 英文别名: (E,2S,4S,8S,10R,11S)-1-[(4R,6R)-6-[(E,3S,4S)-4-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethylhex-1-enyl]-2,2-dimethyl-1,3-dioxan-4-yl]-4-hydroxy-13-iodo-2,8-bis[(4-methoxyphenyl)methoxy]-11-methyl-10-tri(propan-2-yl)silyloxytridec-12-en-6-one
• CAS: 332179-92-7
• 化学式: C₅₉H₉₉IO₁₀Si₂
• 分子量: 1151.5
• InChiKey: IFZCJMYUQNZSHM-UOJSZGIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.35
• 重原子数：
  72
• 可旋转键数：
  32
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (E)-(2S,4S,8S,10R,11S)-1-{(4R,6R)-6-[(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-4-hydroxy-13-iodo-2,8-bis-(4-methoxy-benzyloxy)-11-methyl-10-triisopropylsilanyloxy-tridec-12-en-6-one 在 tetramethylammonium triacetoxyborohydride 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 反应 18.0h， 以88%的产率得到(E)-(2S,4R,6R,8R,10R,11S)-1-{(4R,6R)-6-[(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-13-iodo-2,8-bis-(4-methoxy-benzyloxy)-11-methyl-10-triisopropylsilanyloxy-tridec-12-ene-4,6-diol
  参考文献：
  名称：

  Remote 1,5-stereoinduction in boron aldol reactions of methyl ketones: application to the convergent assembly of the 1,3-polyol sequence of (+)-roxaticin

  摘要：

  By exploiting 1,5-anti stereoinduction in the boron aldol coupling of the beta -alkoxy methyl ketones 6 and 8 with aldehydes 7 and 9, the convergent synthesis of 2, corresponding to the fully protected polyol sequence of the 30-membered macrolide, (+)-roxaticin (1), was achieved in an efficient manner (15 steps and 24.0% yield from ketone 15). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02205-x
• 作为产物：
  描述：

  (E)-(4S,6R,7S)-9-Iodo-4-(4-methoxy-benzyloxy)-7-methyl-6-triisopropylsilanyloxy-non-8-en-2-one 、 (3R)-4-[(4R,6R)-6-[(E,3S,4S)-4-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethylhex-1-enyl]-2,2-dimethyl-1,3-dioxan-4-yl]-3-[(4-methoxyphenyl)methoxy]butanal 在 氯代二环己基硼烷 、 三乙胺 、 双氧水 作用下， 以 乙醚 、 甲醇 为溶剂， 反应 16.17h， 以53%的产率得到(E)-(2S,4S,8S,10R,11S)-1-{(4R,6R)-6-[(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-4-hydroxy-13-iodo-2,8-bis-(4-methoxy-benzyloxy)-11-methyl-10-triisopropylsilanyloxy-tridec-12-en-6-one
  参考文献：
  名称：

  Remote 1,5-stereoinduction in boron aldol reactions of methyl ketones: application to the convergent assembly of the 1,3-polyol sequence of (+)-roxaticin

  摘要：

  By exploiting 1,5-anti stereoinduction in the boron aldol coupling of the beta -alkoxy methyl ketones 6 and 8 with aldehydes 7 and 9, the convergent synthesis of 2, corresponding to the fully protected polyol sequence of the 30-membered macrolide, (+)-roxaticin (1), was achieved in an efficient manner (15 steps and 24.0% yield from ketone 15). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02205-x