(2R,S,5S)-5-<1(R)-<(tert-Butyldiphenylsilyl)oxy>-ethyl>-2-methoxytetrahydrofuran | 130258-61-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2R,S,5S)-5-<1(R)-<(tert-Butyldiphenylsilyl)oxy>-ethyl>-2-methoxytetrahydrofuran
• 英文别名: tert-butyl-[(1R)-1-[(2S)-5-methoxyoxolan-2-yl]ethoxy]-diphenylsilane
• CAS: 130258-61-6；130323-46-5；130324-85-5
• 化学式: C₂₃H₃₂O₃Si
• 分子量: 384.591
• InChiKey: OAHDEVSVECUYQC-LJDIEGPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,S,5S)-5-<1(R)-<(tert-Butyldiphenylsilyl)oxy>-ethyl>-2-methoxytetrahydrofuran 在 三氟化硼乙醚 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 2,2-Dimethyl-propionic acid 2-((2R,3S,6R)-6-{(E)-3-[(2R,5S)-5-((R)-1-hydroxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-ethyl ester
  参考文献：
  名称：

  Total synthesis of tetronomycin

  摘要：

  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.

  DOI：

  10.1021/jo00036a026
• 作为产物：
  描述：

  (E)-(4R,5S)-4-Acetoxy-5-(methanesulfonyloxy)-2-hexenal 以 甲醇 为溶剂， 生成 (2R,S,5S)-5-<1(R)-<(tert-Butyldiphenylsilyl)oxy>-ethyl>-2-methoxytetrahydrofuran
  参考文献：
  名称：

  Syntheses of the tetrahydrofuran subunits of tetronasin and tetronomycin.

  摘要：

  L-Rhamnal 已转化为四氢呋喃亚基（14 和 21）的四氢萘欣（ICI-139603）（1）和四氢霉素（2），其中位于 2 和 5 位的三个手性中心以及含甲氧基的碳具有镜像。

  DOI：

  10.1248/cpb.38.1778

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：——