(4S,5R)-5-((R)-4-(tert-butyldiphenylsilanyloxy)pentyl)-2,2-dimethyl-1,3-dioxolane-4-carboxaldehyde | 1388144-84-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5R)-5-((R)-4-(tert-butyldiphenylsilanyloxy)pentyl)-2,2-dimethyl-1,3-dioxolane-4-carboxaldehyde
• 英文别名: (4S,5R)-5-[(4R)-4-[tert-butyl(diphenyl)silyl]oxypentyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
• CAS: 1388144-84-0
• 化学式: C₂₇H₃₈O₄Si
• 分子量: 454.682
• InChiKey: BHSPIHASZYRZDF-NQHRYMMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5R)-5-((R)-4-(tert-butyldiphenylsilanyloxy)pentyl)-2,2-dimethyl-1,3-dioxolane-4-carboxaldehyde 在 titanium(IV) isopropylate 、 S-1,1'-联-2-萘酚 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 73.0h， 生成 ((R)-5-((4R,5R)-5-((S)-1-(methoxymethoxy)but-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pentan-2-yloxy)(tert-butyl)diphenylsilane
  参考文献：
  名称：

  Asymmetric total synthesis of 5′-epi-paecilomycin-F

  摘要：

  The asymmetric total synthesis of one of the stereoisomers of the naturally occurring 14-membered ring macrolide paecilomycin-F (5'-epi) has been reported in this article. The main highlight of the synthetic strategy involves the successful application of a ring closing metathesis (RCM) reaction at a late stage. Asymmetric Keck allylation, Sharpless asymmetric dihydroxylation, and Mitsunobu esterification have also been used successfully for the total synthesis of 5'-epi-paecilomycin-F. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.05.017
• 作为产物：
  描述：

  (5R)-5-[1-(tert-butyl)-1,1-diphenylsilyl]oxyhexanal 在 甲基磺酰胺 、 AD-mix-β 、 sodium hydride 、 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 乙醚 、 二氯甲烷 、 水 、 甲苯 、 mineral oil 、 叔丁醇 为溶剂， 反应 6.17h， 生成 (4S,5R)-5-((R)-4-(tert-butyldiphenylsilanyloxy)pentyl)-2,2-dimethyl-1,3-dioxolane-4-carboxaldehyde
  参考文献：
  名称：

  Asymmetric total synthesis of 5′-epi-paecilomycin-F

  摘要：

  The asymmetric total synthesis of one of the stereoisomers of the naturally occurring 14-membered ring macrolide paecilomycin-F (5'-epi) has been reported in this article. The main highlight of the synthetic strategy involves the successful application of a ring closing metathesis (RCM) reaction at a late stage. Asymmetric Keck allylation, Sharpless asymmetric dihydroxylation, and Mitsunobu esterification have also been used successfully for the total synthesis of 5'-epi-paecilomycin-F. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.05.017

文献信息

• Asymmetric total synthesis of 5′-epi-paecilomycin-F
  作者：Nandan Jana、Samik Nanda

  DOI：10.1016/j.tetasy.2012.05.017

  日期：2012.5

  The asymmetric total synthesis of one of the stereoisomers of the naturally occurring 14-membered ring macrolide paecilomycin-F (5'-epi) has been reported in this article. The main highlight of the synthetic strategy involves the successful application of a ring closing metathesis (RCM) reaction at a late stage. Asymmetric Keck allylation, Sharpless asymmetric dihydroxylation, and Mitsunobu esterification have also been used successfully for the total synthesis of 5'-epi-paecilomycin-F. (C) 2012 Elsevier Ltd. All rights reserved.