(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 | 332179-79-0

• 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: (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
• CAS: 332179-79-0
• 化学式: C₃₂H₅₄O₆Si
• 分子量: 562.863
• InChiKey: LTRDLDIIVRLWIX-CKXRYIAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.71
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (R)-1-((tert-butyldimethylsilyl)oxy)hex-5-en-3-ol 在 草酰氯 、 四丁基氟化铵 、 氧气 、 trityl tetrafluoroborate 、 4-甲基苯磺酸吡啶 、 二甲基亚砜 、 三乙胺 、 copper(l) chloride 、 palladium dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 (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
  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

文献信息

• Remote 1,5-stereoinduction in boron aldol reactions of methyl ketones: application to the convergent assembly of the 1,3-polyol sequence of (+)-roxaticin
  作者：Ian Paterson、Lynne A. Collett

  DOI：10.1016/s0040-4039(00)02205-x

  日期：2001.2

  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.