(2R,3S,6R)-6-Formyl-3-methyl-2-<2-(trimethylacetoxy)ethyl>tetrahydropyran | 130258-57-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (2R,3S,6R)-6-Formyl-3-methyl-2-<2-(trimethylacetoxy)ethyl>tetrahydropyran
• 英文别名: 2-[(2R,3S,6R)-6-formyl-3-methyloxan-2-yl]ethyl 2,2-dimethylpropanoate
• CAS: 130258-57-0
• 化学式: C₁₄H₂₄O₄
• 分子量: 256.342
• InChiKey: HJDXTZRVTODCGM-QJPTWQEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S,6R)-6-Formyl-3-methyl-2-<2-(trimethylacetoxy)ethyl>tetrahydropyran 在 氯化亚砜 、 三氟化硼乙醚 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 2,2-Dimethyl-propionic acid 2-((2R,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-ethyl ester
  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：

  (2R,3S,6R)-6-<<(tert-Butyldimethylsilyl)oxy>methyl>-2-(2-hydroxyethyl)-3-methyltetrahydropyran 生成 (2R,3S,6R)-6-Formyl-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

文献信息

• Synthesis of the polyether fragment A/B-ring system of tetronomycin.
  作者：Kozo HORI、Keiichi NOMURA、Naotsuka HIKAGE、Eiichi YOSHII

  DOI：10.1248/cpb.38.1781

  日期：——

  The polyether fragment 18 of tetronomycin (1) that contains the tetrahydrofuryl and tetrahydropyranyl groups has been synthesized via a Lewis acid-catalyzed coupling of a 2-methoxytetrahydrofuran 16 with a 2-(1-trimethylsilyl-2-propen-1-yl)tetrahydropyran 15.

  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。
• HORI, KOZO;NOMURA, KEIICHI;HIKAGE, NAOTSUKA;YOSHII, EIICHI, CHEM. AND PHARM. BULL., 38,(1990) N, C. 1781-1783
  作者：HORI, KOZO、NOMURA, KEIICHI、HIKAGE, NAOTSUKA、YOSHII, EIICHI

  DOI：——

  日期：——
• 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.