(4S,5R)-4-Methyl-3-<(5R)-2-methyl-5,6-(isopropylidenedioxy)hexanoyl>-5-phenyl-1,3-oxazolidin-2-one | 130258-50-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5R)-4-Methyl-3-<(5R)-2-methyl-5,6-(isopropylidenedioxy)hexanoyl>-5-phenyl-1,3-oxazolidin-2-one
• CAS: 130258-50-3；130323-44-3
• 化学式: C₂₀H₂₇NO₅
• 分子量: 361.438
• InChiKey: QFDYSQUXWXANLQ-NXOUSBOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4S,5R)-4-Methyl-3-<(5R)-2-methyl-5,6-(isopropylidenedioxy)hexanoyl>-5-phenyl-1,3-oxazolidin-2-one 在 盐酸 、 三乙基硅烷 、 lithium hydroxide 、 三氟化硼乙醚 、 双氧水 、 二异丁基氢化铝 作用下， 生成 (2R,3S,6R)-6-<<(tert-Butyldimethylsilyl)oxy>methyl>-3-methyl-2-<2-(trimethylacetoxy)ethyl>tetrahydropyran
  参考文献：
  名称：

  Synthesis of the polyether fragment A/B-ring system of tetronomycin.

  摘要：

  通过路易斯酸催化2-甲氧基四氢呋喃16与2-(1-三甲基硅烷基-2-丙烯-1-基)四氢吡喃15的偶联反应，合成了含有四氢呋喃基和四氢吡喃基的聚醚片段18。

  DOI：

  10.1248/cpb.38.1781
• 作为产物：
  描述：

  (R)-4-(2,2-dimethyl-1,3-dioxolan-4-yl)butyric acid 在 4-二甲氨基吡啶 、 sodium hexamethyldisilazane 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 (4S,5R)-4-Methyl-3-<(5R)-2-methyl-5,6-(isopropylidenedioxy)hexanoyl>-5-phenyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Synthesis of the polyether fragment A/B-ring system of tetronomycin.

  摘要：

  通过路易斯酸催化2-甲氧基四氢呋喃16与2-(1-三甲基硅烷基-2-丙烯-1-基)四氢吡喃15的偶联反应，合成了含有四氢呋喃基和四氢吡喃基的聚醚片段18。

  DOI：

  10.1248/cpb.38.1781

文献信息

• Total synthesis of tetronomycin
  作者：Kozo Hori、Naotsuka Hikage、Atsushi Inagaki、Shuho Mori、Keiichi Nomura、Eiichi Yoshii

  DOI：10.1021/jo00036a026

  日期：1992.5

  The first total synthesis of (+)-tetronomycin (1), a novel tetronic acid ionophore antibiotic, has been achieved through the synthesis and assemblage of the four cyclic segments 4, 5, 7, and 8. Construction of the C5-C-13 cyclohexyl portion 5 involves as the key step either a Beckmann fragmentation of the bicyclic ketone oxime 45 or an L-Selectride-mediated reductive annulation of the nona-2,7-dienoate 53. The C-14-C28 polyether fragment 6 was constructed by a BF3-catalyzed coupling reaction of the C-14-C22 allylsilane 7 and the C23-C28 tetrahydrofuran 8 which were derived, respectively, from L-ascorbic acid or (R)-3-hydroxyisobutyrate and L-rhamnal. The union of 5 and 6 by an aldol condensation, followed by photoisomerization of the derived diastereomeric alpha,beta-unsaturated esters, provided (Z)-61, which was converted to the aldehyde 63. Subsequent acylation of the tetronate 4 with 63 via an aldol reaction-oxidation sequence afforded the protected tetronomycin 64. Final deprotection provided synthetic tetronomycin, which was characterized as its sodium salt.