n-butyl (2R,3S)-2-hydroxy-3-methyl-5-trimethylsilyl-4-pentynoate | 1158183-83-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: n-butyl (2R,3S)-2-hydroxy-3-methyl-5-trimethylsilyl-4-pentynoate
• 英文别名: butyl (2R,3S)-2-hydroxy-3-methyl-5-trimethylsilylpent-4-ynoate
• CAS: 1158183-83-5
• 化学式: C₁₃H₂₄O₃Si
• 分子量: 256.417
• InChiKey: AMJZQLFZZVQQBX-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  n-butyl (2R,3S)-2-hydroxy-3-methyl-5-trimethylsilyl-4-pentynoate 、 碘甲烷 在 silver(l) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以64%的产率得到n-butyl (2R,3S)-3-methyl-2-methoxy-5-trimethylsilyl-4-pentynoate
  参考文献：
  名称：

  First synthesis of (+)-myxothiazol A

  摘要：

  First convergent synthesis of (+)-myxothiazol A(1) was achieved based on modified (one-pot) Julia Olefination between (3,5R)-dimethoxy-(4R)-methyl 6-oxo-(2E)-hexenamide (2), corresponding to left-side of the final molecule, and E-4-2'-(1S,6-dimethylheptadiene)-(2,4'-bis-thiazole)-4-methybenzothiazole sulfone (4) corresponding to right-side. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.125
• 作为产物：
  描述：

  3-甲基-2-(2R,3S)-环氧乙烷羧酸丁酯 、 三甲基乙炔基硅 在 正丁基锂 、 氯化二乙基铝 作用下， 以 四氢呋喃 为溶剂， 以72%的产率得到n-butyl (2R,3S)-2-hydroxy-3-methyl-5-trimethylsilyl-4-pentynoate
  参考文献：
  名称：

  First synthesis of (+)-myxothiazol A

  摘要：

  First convergent synthesis of (+)-myxothiazol A(1) was achieved based on modified (one-pot) Julia Olefination between (3,5R)-dimethoxy-(4R)-methyl 6-oxo-(2E)-hexenamide (2), corresponding to left-side of the final molecule, and E-4-2'-(1S,6-dimethylheptadiene)-(2,4'-bis-thiazole)-4-methybenzothiazole sulfone (4) corresponding to right-side. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.125

文献信息

• Total synthesis of (+)-myxothiazols A and Z
  作者：Yuki Iwaki、Masahiro Kaneko、Hiroyuki Akita

  DOI：10.1016/j.tetasy.2008.12.031

  日期：2009.2

  The first synthesis of (+)-myxothiazol A 1 was achieved based on a modified Julia olefination between (3,5R)-dimethoxy-(4R)-methyl-6-oxo-(2E)-hexenamide 3, corresponding to the left side of the final molecule, and 4-(2 ''-benzothiazolyl)sulfonylmethyl-2'-[(1'''R),6"'-dimethylhepta-(2"'E),(4"'E)-dienyl]-2,4'-bithiazole 6, corresponding to the right side. The synthesis of (+)-myxothiazol Z 2 was also achieved based on modified Julia olefination between (3,5R)-dimethoxy-(4R)-methyl-6-oxo-(2E)-hexenoate 4, corresponding to left side of the final molecule, and (S)-sulfone 6. (C) 2009 Elsevier Ltd. All rights reserved.