(3R,4S,7S,8R)-9-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-7-hydroxy-4,8-dimethyl-nonanoic acid | 214273-41-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (3R,4S,7S,8R)-9-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-7-hydroxy-4,8-dimethyl-nonanoic acid
• 英文别名: (3R,4S,7S,8R)-3-[tert-butyl(diphenyl)silyl]oxy-7-hydroxy-4,8-dimethyl-9-phenylmethoxynonanoic acid
• CAS: 214273-41-3
• 化学式: C₃₄H₄₆O₅Si
• 分子量: 562.822
• InChiKey: WQNWIWNTUDZSAS-PSQNISHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.04
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4S,7S,8R)-9-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-7-hydroxy-4,8-dimethyl-nonanoic acid 在 silver tetrafluoroborate 、 三苯基膦 作用下， 以 甲苯 为溶剂， 以41%的产率得到(4R,5S,8S)-8-((R)-2-Benzyloxy-1-methyl-ethyl)-4-(tert-butyl-diphenyl-silanyloxy)-5-methyl-oxocan-2-one
  参考文献：
  名称：

  Stereoselective reduction of α′-branched α,β-ynones. Application to the synthesis of the Octalactin A ring

  摘要：

  A flexible, efficient route to chiral 3-hydroxy-4-methyl- and 3-hydroxy-4-methoxyalkanoic acids, with high control of the C(3) configuration, has been disclosed, which is based on the borane-mediated reduction of 1-trimethylsilyl-1-alkyn-3-ones (6) in the presence of oxazaborolidine 7 followed by hydroboration of the resulting propargylic alcohols 4 and 5. This strategy has been applied to the synthesis of the Octalactin A ring. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01420-8
• 作为产物：
  描述：

  2,2-Dimethyl-propionic acid (1S,4S)-1-((R)-2-benzyloxy-1-methyl-ethyl)-5-(tert-butyl-diphenyl-silanyloxy)-4-methyl-pentyl ester 在 咪唑 、 dimethyl sulfide borane 、 chiral oxazaborolidine (S config.) 、 四丁基氟化铵 、 二异丁基氢化铝 、 碳酸氢钠 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (3R,4S,7S,8R)-9-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-7-hydroxy-4,8-dimethyl-nonanoic acid
  参考文献：
  名称：

  Stereoselective reduction of α′-branched α,β-ynones. Application to the synthesis of the Octalactin A ring

  摘要：

  A flexible, efficient route to chiral 3-hydroxy-4-methyl- and 3-hydroxy-4-methoxyalkanoic acids, with high control of the C(3) configuration, has been disclosed, which is based on the borane-mediated reduction of 1-trimethylsilyl-1-alkyn-3-ones (6) in the presence of oxazaborolidine 7 followed by hydroboration of the resulting propargylic alcohols 4 and 5. This strategy has been applied to the synthesis of the Octalactin A ring. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01420-8

文献信息

• Stereoselective reduction of α′-branched α,β-ynones. Application to the synthesis of the Octalactin A ring
  作者：Jordi Bach、Jordi Garcia

  DOI：10.1016/s0040-4039(98)01420-8

  日期：1998.9

  A flexible, efficient route to chiral 3-hydroxy-4-methyl- and 3-hydroxy-4-methoxyalkanoic acids, with high control of the C(3) configuration, has been disclosed, which is based on the borane-mediated reduction of 1-trimethylsilyl-1-alkyn-3-ones (6) in the presence of oxazaborolidine 7 followed by hydroboration of the resulting propargylic alcohols 4 and 5. This strategy has been applied to the synthesis of the Octalactin A ring. (C) 1998 Elsevier Science Ltd. All rights reserved.