(3R,5S,6R)-3-hydroxy-5-methoxymethoxy-6,9-dimethyl-dec-8-enoic acid tert-butyl ester | 312962-18-8

• 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: (3R,5S,6R)-3-hydroxy-5-methoxymethoxy-6,9-dimethyl-dec-8-enoic acid tert-butyl ester
• 英文别名: tert-butyl (3R,5S,6R)-3-hydroxy-5-(methoxymethoxy)-6,9-dimethyldec-8-enoate
• CAS: 312962-18-8
• 化学式: C₁₈H₃₄O₅
• 分子量: 330.465
• InChiKey: QGOMPXKSBPAOAD-OAGGEKHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,5S,6R)-3-hydroxy-5-methoxymethoxy-6,9-dimethyl-dec-8-enoic acid tert-butyl ester 在 咪唑 、 lithium aluminium tetrahydride 、 sodium hydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.75h， 生成 2-allyl-6-(tert-butyl-dimethyl-silanyloxy)-benzoic acid (1R,3S,4R)-1-[2-(4-methoxy-benzyloxy)-ethyl]-3-methoxymethoxy-4,7-dimethyl-oct-6-enyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of the Fully Functional Macrolide Core of Salicylihalamide:  Remote Control of Olefin Geometry during RCM

  摘要：

  [GRAPHICS]A catalysis-based approach to the core region 24 of the antitumor agents salicylihalamides A and B is reported. Key steps are two asymmetric hydrogenations of beta -keto esters 13 and 16 catalyzed by [(R)-BINAP-RuCl2](2). NEt3 and an RCM-based macrocyclization effected by the NHC-containing ruthenium carbene 21. The stereochemical outcome of the tatter reaction is controlled by remote substituents on the phenolic OH group of the cyclization precursor 23.

  DOI：

  10.1021/ol006646d
• 作为产物：
  描述：

  (3S,4R)-3-methoxymethoxy-4,7-dimethyl-oct-6-enoic acid methyl ester 在 [(R)-BINAP*RuCl₂]*NEt₃ 氢气 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 为溶剂， -45.0~25.0 ℃ 、8.11 MPa 条件下， 反应 11.0h， 生成 (3R,5S,6R)-3-hydroxy-5-methoxymethoxy-6,9-dimethyl-dec-8-enoic acid tert-butyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of the Fully Functional Macrolide Core of Salicylihalamide:  Remote Control of Olefin Geometry during RCM

  摘要：

  [GRAPHICS]A catalysis-based approach to the core region 24 of the antitumor agents salicylihalamides A and B is reported. Key steps are two asymmetric hydrogenations of beta -keto esters 13 and 16 catalyzed by [(R)-BINAP-RuCl2](2). NEt3 and an RCM-based macrocyclization effected by the NHC-containing ruthenium carbene 21. The stereochemical outcome of the tatter reaction is controlled by remote substituents on the phenolic OH group of the cyclization precursor 23.

  DOI：

  10.1021/ol006646d

文献信息

• Asymmetric Synthesis of the Fully Functional Macrolide Core of Salicylihalamide:  Remote Control of Olefin Geometry during RCM
  作者：Alois Fürstner、Oliver R. Thiel、Gaetano Blanda

  DOI：10.1021/ol006646d

  日期：2000.11.1

  [GRAPHICS]A catalysis-based approach to the core region 24 of the antitumor agents salicylihalamides A and B is reported. Key steps are two asymmetric hydrogenations of beta -keto esters 13 and 16 catalyzed by [(R)-BINAP-RuCl2](2). NEt3 and an RCM-based macrocyclization effected by the NHC-containing ruthenium carbene 21. The stereochemical outcome of the tatter reaction is controlled by remote substituents on the phenolic OH group of the cyclization precursor 23.