(3S,4S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-((4R,5S,6R)-6-isopropyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-7-methoxy-3-methyl-5-methylene-octan-2-one | 161985-49-5

• 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: (3S,4S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-((4R,5S,6R)-6-isopropyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-7-methoxy-3-methyl-5-methylene-octan-2-one
• 英文别名: (3S,4S,6R,7S)-6-[tert-butyl(dimethyl)silyl]oxy-4-hydroxy-7-methoxy-3-methyl-5-methylidene-8-phenylmethoxy-1-[(4R,5S,6R)-2,2,5-trimethyl-6-propan-2-yl-1,3-dioxan-4-yl]octan-2-one
• CAS: 161985-49-5
• 化学式: C₃₄H₅₈O₇Si
• 分子量: 606.916
• InChiKey: LOFCNOJPYLXHLD-KGVCUJDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.93
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3S,4S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-((4R,5S,6R)-6-isopropyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-7-methoxy-3-methyl-5-methylene-octan-2-one 在 Wilkinson's catalyst 氢气 作用下， 以 苯 为溶剂， 反应 16.0h， 以96%的产率得到(3S,4R,5S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-((4R,5S,6R)-6-isopropyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-7-methoxy-3,5-dimethyl-octan-2-one
  参考文献：
  名称：

  Stereocontrolled aldol additions to α-methylene-β-alkoxy aldehydes: Application to the synthesis of a C13C25 segment of bafilomycin A1

  摘要：

  A boron-mediated, syn-aldol coupling between ethyl ketone 8 and aldehyde 9, followed by directed hydrogenation at C-16 and acetonide hydrolysis, gives the C-13-C-25 segment 6 of bafilomycin A(1).

  DOI：

  10.1016/0040-4039(94)02205-p
• 作为产物：
  描述：

  (2R,3R)-2,4-dimethyl-3-[(tert-butyldimethylsilyl)oxy]pentanal 在 sodium periodate 、 四氧化锇 、 N-甲基吲哚酮 、 三氟甲磺酸二丁硼 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 四氯化钛 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.84h， 生成 (3S,4S,6R,7S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-((4R,5S,6R)-6-isopropyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-7-methoxy-3-methyl-5-methylene-octan-2-one
  参考文献：
  名称：

  Stereocontrolled aldol additions to α-methylene-β-alkoxy aldehydes: Application to the synthesis of a C13C25 segment of bafilomycin A1

  摘要：

  A boron-mediated, syn-aldol coupling between ethyl ketone 8 and aldehyde 9, followed by directed hydrogenation at C-16 and acetonide hydrolysis, gives the C-13-C-25 segment 6 of bafilomycin A(1).

  DOI：

  10.1016/0040-4039(94)02205-p

文献信息

• Stereocontrolled aldol additions to α-methylene-β-alkoxy aldehydes: Application to the synthesis of a C13C25 segment of bafilomycin A1
  作者：Ian Paterson、Shelley Bower、Malcolm D. McLeod

  DOI：10.1016/0040-4039(94)02205-p

  日期：1995.1

  A boron-mediated, syn-aldol coupling between ethyl ketone 8 and aldehyde 9, followed by directed hydrogenation at C-16 and acetonide hydrolysis, gives the C-13-C-25 segment 6 of bafilomycin A(1).