(R)-6-benzyloxy-3-hydroxy-hexanoic acid methylester | 87894-27-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-6-benzyloxy-3-hydroxy-hexanoic acid methylester
• 英文别名: (-)-6-benzyloxy-3-hydroxyhexanoic acid methyl ester；Methyl (3R)-3-hydroxy-6-(phenylmethoxy)hexanoate；methyl (3R)-3-hydroxy-6-phenylmethoxyhexanoate
• CAS: 87894-27-7
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: XGHAGEQKXHMMTN-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-6-benzyloxy-3-hydroxy-hexanoic acid methylester 生成 methyl (3R)-3,6-bis[[tert-butyl(dimethyl)silyl]oxy]hexanoate
  参考文献：
  名称：

  HIRAMA, MASAHIRO;SHIMIZU, MITSUAKI;IWASHITA, MITSUKO, J. CHEM. SOC. CHEM. COMMUN., 1983, 10, 599-600

  摘要：

  DOI：
• 作为产物：
  描述：

  Potassium; 6-benzyloxy-3-oxo-hexanoate 以51%的产率得到
  参考文献：
  名称：

  HIRAMA, MASAHIRO;SHIMIZU, MITSUAKI;IWASHITA, MITSUKO, J. CHEM. SOC. CHEM. COMMUN., 1983, 10, 599-600

  摘要：

  DOI：

文献信息

• Diastereoselective and convergent synthesis of both 11′-epimers of (−)-(2R,3R,6S)-carnavaline
  作者：Axel Pahl、Jörg Oetting、Jens Holzkamp、Hartmut H. Meyer

  DOI：10.1016/s0040-4020(97)00428-6

  日期：1997.5

  Enantio- and diastereoselective syntheses of both 11′-epimers of (−)-carnavaline 1 have been achieved. Since the configuration of the remote chiral centre in the C-12 side chain of naturally occurring (−)-carnavaline had been unknown and spectroscopic data were not conclusive, an assignment of the 11′S-epimer to the natural product by comparison of the melting points is discussed and complete spectroscopic

  （-）-carnavaline 1的11'-受体的对映异构和非对映选择性合成均已实现。由于在天然存在的C-12侧链上的远程手性中心的构型（ - ） - carnavaline已未知和光谱数据不是结论性的，则11'的分配š差向异构体的天然产物的比较讨论了熔点并给出了完整的光谱数据。
• Enantiospecific syntheses of trifunctional (R)-3-hydroxy esters by baker's yeast reduction
  作者：Masahiro Hirama、Mitsuaki Shimizu、Mitsuko Iwashita

  DOI：10.1039/c39830000599

  日期：——

  Asymmetric syntheses of the enantiomerically pure trifunctional (R)-3-hydroxy esters (7)–(10) can be achieved by baker's yeast reduction of the hydrolysed β-keto carboxylates (2)–(5) instead of by reduction of the corresponding ester.

  对映体纯的三官能（R）-3-羟基酯（7）–（10）的不对称合成可以通过面包酵母还原水解的β-酮羧酸盐（2）–（5）来实现，而不是通过还原相应的酯。
• Total synthesis of the piperidinol alkaloid (−)-(2R,3R,6S)-cassine
  作者：Jörg Oetting、Jens Holzkamp、Hartmut H. Meyer、Axel Pahl

  DOI：10.1016/s0957-4166(96)00537-x

  日期：1997.2

  A highly efficient, flexible and diastereoselective route to all-cis-2,6-disubstituted 3-piperidinols has been accomplished. The key component of the synthesis is a chiral beta-hydroxyester, which was obtained by lipase catalyzed kinetic resolution. Based on this starting material, diastereoselective alkylation of its dianion, Curtius rearrangement to a 2-oxazolidinone, Grignard reaction to introduce the side-chain and conversion of the aliphatic 2-oxazolidinone into a 3-piperidinol by imine cyclization lead to the exemplary total synthesis of naturally occurring (-)-(2R,3R,6S)-cassine. (C) 1997 Elsevier Science Ltd. All rights reserved.