methyl (4R,5R)-6-tert-butyldimethylsilyloxy-3,5-dimethoxy-4-methyl-2(E)-hexenamide | 1093126-40-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (4R,5R)-6-tert-butyldimethylsilyloxy-3,5-dimethoxy-4-methyl-2(E)-hexenamide
• 英文别名: (E,4R,5R)-6-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethoxy-4-methylhex-2-enamide
• CAS: 1093126-40-9
• 化学式: C₁₅H₃₁NO₄Si
• 分子量: 317.501
• InChiKey: BDVNSCOITMKISH-XLCKQVHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (4R,5R)-6-tert-butyldimethylsilyloxy-3,5-dimethoxy-4-methyl-2(E)-hexenamide 在 氟化氢吡啶 、 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 以32%的产率得到(3,5SR)-dimethoxy-(4RS)-methyl-6-oxo-2-E-hexenamide
  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：

  在 N-羟基-7-氮杂苯并三氮唑 、 carbodiimide hydrochloride 、 三乙胺 、 氨 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 生成 methyl (4R,5R)-6-tert-butyldimethylsilyloxy-3,5-dimethoxy-4-methyl-2(E)-hexenamide
  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.