(2R,3S)-2-[(2R,3R,4S,5S,6S)-6-methoxy-3,5-dimethyl-4-phenylmethoxyoxan-2-yl]pentan-3-ol | 1242057-40-4

• 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: (2R,3S)-2-[(2R,3R,4S,5S,6S)-6-methoxy-3,5-dimethyl-4-phenylmethoxyoxan-2-yl]pentan-3-ol
• CAS: 1242057-40-4
• 化学式: C₂₀H₃₂O₄
• 分子量: 336.472
• InChiKey: SKDIKYAFJZCMBY-KGUMHCDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-[(2R,3R,4S,5S,6S)-6-methoxy-3,5-dimethyl-4-phenylmethoxyoxan-2-yl]pentan-3-ol 、 乙酸酐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以95%的产率得到[(2R,3S)-2-[(2R,3R,4S,5S,6S)-6-methoxy-3,5-dimethyl-4-phenylmethoxyoxan-2-yl]pentan-3-yl] acetate
  参考文献：
  名称：

  Synthesis of C15–C27 segment of venturicidine X by utilizing desymmetrization protocol

  摘要：

  We have achieved the synthesis of C15-C27 fragment of venturicidine X using desymmetrization protocol, substrate-controlled Grignard reaction, Barton-McCombie reaction, Sharpless epoxidation, and TBSOTf-mediated rearrangement to produce the aldol product through a non-aldol route as the key step following 23 longest linear sequences with 6.4% overall yield starting from a known intermediate 11. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.148
• 作为产物：
  描述：

  (2S)-2-((2S,3R,4S,5S)-4-(benzyloxy)-6-methoxy-3,5-dimethyl-tetrahydro-2H-pyran-2-yl)propanal 、 乙基溴化镁 以 四氢呋喃 为溶剂， 反应 1.0h， 以89%的产率得到(2R,3S)-2-[(2R,3R,4S,5S,6S)-6-methoxy-3,5-dimethyl-4-phenylmethoxyoxan-2-yl]pentan-3-ol
  参考文献：
  名称：

  Synthesis of C15–C27 segment of venturicidine X by utilizing desymmetrization protocol

  摘要：

  We have achieved the synthesis of C15-C27 fragment of venturicidine X using desymmetrization protocol, substrate-controlled Grignard reaction, Barton-McCombie reaction, Sharpless epoxidation, and TBSOTf-mediated rearrangement to produce the aldol product through a non-aldol route as the key step following 23 longest linear sequences with 6.4% overall yield starting from a known intermediate 11. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.148

文献信息

• Synthesis of C15–C27 segment of venturicidine X by utilizing desymmetrization protocol
  作者：J.S. Yadav、Sk. Samad Hossain、Debendra K. Mohapatra

  DOI：10.1016/j.tetlet.2010.05.148

  日期：2010.8

  We have achieved the synthesis of C15-C27 fragment of venturicidine X using desymmetrization protocol, substrate-controlled Grignard reaction, Barton-McCombie reaction, Sharpless epoxidation, and TBSOTf-mediated rearrangement to produce the aldol product through a non-aldol route as the key step following 23 longest linear sequences with 6.4% overall yield starting from a known intermediate 11. (C) 2010 Elsevier Ltd. All rights reserved.