(2S,4R)-5-[tert-butyl(diphenyl)silyl]oxy-4-methoxy-2-methylpentanal | 725250-94-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S,4R)-5-[tert-butyl(diphenyl)silyl]oxy-4-methoxy-2-methylpentanal
• CAS: 725250-94-2
• 化学式: C₂₃H₃₂O₃Si
• 分子量: 384.591
• InChiKey: GEJMRNMETJGPGE-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,4R)-5-[tert-butyl(diphenyl)silyl]oxy-4-methoxy-2-methylpentanal 在 barium dihydroxide 、 lithium hydroxide 、 草酰氯 、 pyridine-SO3 complex 、 dimethyl sulfide borane 、 CBS catalyst 、 四丁基氟化铵 、 双(三甲基硅烷基)氨基钾 、 sodium hydride 、 LiDBB 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 溶剂黄146 、 二甲基亚砜 为溶剂， 生成 methyl (2E,4E)-6-[(4R,5R,6R)-6-[(2R,5S,6E,9R,11R,12E)-14-[(4S,5R,6S)-6-[(2S)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl]-5,11-dimethoxy-6,9-dimethyltetradeca-6,12-dien-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl]hexa-2,4-dienoate
  参考文献：
  名称：

  Synthesis of the C1–C27 portion of the aplyronines

  摘要：

  This manuscript describes the use of the anti,anti-diastereoselective aldol reaction of an efficiently generated dipropionate equivalent to construct the C-5-C-14-portion of the aplyronines. This portion was then coupled with a compound corresponding to C-15-G(20) of the targets. Further elaboration and an additional coupling led to an intermediate containing C-1-C-27 with appropriate stereochemistry and functionalization for eventual conversion into the aplyronines. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.159
• 作为产物：
  描述：

  (2S,4R)-5-[tert-butyl(diphenyl)silyl]oxy-N,4-dimethoxy-N,2-dimethylpentanamide 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,4R)-5-[tert-butyl(diphenyl)silyl]oxy-4-methoxy-2-methylpentanal
  参考文献：
  名称：

  Synthesis of the C1–C27 portion of the aplyronines

  摘要：

  This manuscript describes the use of the anti,anti-diastereoselective aldol reaction of an efficiently generated dipropionate equivalent to construct the C-5-C-14-portion of the aplyronines. This portion was then coupled with a compound corresponding to C-15-G(20) of the targets. Further elaboration and an additional coupling led to an intermediate containing C-1-C-27 with appropriate stereochemistry and functionalization for eventual conversion into the aplyronines. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.159

文献信息

• Synthesis of the C1–C27 portion of the aplyronines
  作者：Michael A Calter、Jianguang Zhou

  DOI：10.1016/j.tetlet.2004.04.159

  日期：2004.6

  This manuscript describes the use of the anti,anti-diastereoselective aldol reaction of an efficiently generated dipropionate equivalent to construct the C-5-C-14-portion of the aplyronines. This portion was then coupled with a compound corresponding to C-15-G(20) of the targets. Further elaboration and an additional coupling led to an intermediate containing C-1-C-27 with appropriate stereochemistry and functionalization for eventual conversion into the aplyronines. (C) 2004 Elsevier Ltd. All rights reserved.