O-[(2S,3R,4S)-1-[tert-butyl(dimethyl)silyl]oxy-4-[(4R,5R,6S)-6-ethyl-2,2,5-trimethyl-1,3-dioxan-4-yl]-2-methylpentan-3-yl] methylsulfanylmethanethioate | 1242057-47-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-[(2S,3R,4S)-1-[tert-butyl(dimethyl)silyl]oxy-4-[(4R,5R,6S)-6-ethyl-2,2,5-trimethyl-1,3-dioxan-4-yl]-2-methylpentan-3-yl] methylsulfanylmethanethioate
• CAS: 1242057-47-1
• 化学式: C₂₃H₄₆O₄S₂Si
• 分子量: 478.833
• InChiKey: NHSPWPMHXYVGBM-IEJRGFGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.88
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  94.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O-[(2S,3R,4S)-1-[tert-butyl(dimethyl)silyl]oxy-4-[(4R,5R,6S)-6-ethyl-2,2,5-trimethyl-1,3-dioxan-4-yl]-2-methylpentan-3-yl] methylsulfanylmethanethioate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 3.0h， 以92%的产率得到tert-butyl-[(2R,4R)-4-[(4S,5R,6S)-6-ethyl-2,2,5-trimethyl-1,3-dioxan-4-yl]-2-methylpentoxy]-dimethylsilane
  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：

  二硫化碳 、 (2S,3R,4R)-1-((tert-butyldimethylsilyl)oxy)-4-((4S,5R,6S)-6-ethyl-2,2,5-trimethyl-1,3-dioxan-4-yl)-2-methylpentan-3-ol 、 碘甲烷 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以87%的产率得到O-[(2S,3R,4S)-1-[tert-butyl(dimethyl)silyl]oxy-4-[(4R,5R,6S)-6-ethyl-2,2,5-trimethyl-1,3-dioxan-4-yl]-2-methylpentan-3-yl] methylsulfanylmethanethioate
  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