(2S,3R)-3-hydroxy-2,5-dimethylhexanoic acid

• 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: (2S,3R)-3-hydroxy-2,5-dimethylhexanoic acid
• 化学式: C₈H₁₆O₃
• 分子量: 160.213
• InChiKey: PCXUDLCCHUMCBM-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (2S,3R)-3-hydroxy-2,5-dimethylhexanoic acid 以 乙醚 为溶剂， 反应 0.5h， 生成 (2S,3R)-3-hydroxy-2,5-dimethyl-hexanoic acid methyl ester
  参考文献：
  名称：

  Chelation-controlled ester-derived titanium enolate aldol reaction: diastereoselective syn-aldols with mono- and bidentate aldehydes

  摘要：

  A chelation-controlled and highly diastereoselective synthesis of syn-aldols is described. Aldol reaction of (S)-valinolderived ester with a variety of aldehydes proceeded with high syn-diastercoselectivities (up to 99:1) and isolated yields (94%). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01113-9
• 作为产物：
  描述：

  (2S,3R)-3-Hydroxy-2,5-dimethyl-hexanoic acid (S)-3-methyl-2-(toluene-4-sulfonylamino)-butyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 生成 (2S,3R)-3-hydroxy-2,5-dimethylhexanoic acid
  参考文献：
  名称：

  Chelation-controlled ester-derived titanium enolate aldol reaction: diastereoselective syn-aldols with mono- and bidentate aldehydes

  摘要：

  A chelation-controlled and highly diastereoselective synthesis of syn-aldols is described. Aldol reaction of (S)-valinolderived ester with a variety of aldehydes proceeded with high syn-diastercoselectivities (up to 99:1) and isolated yields (94%). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01113-9

文献信息

• Ester derived titanium enolate aldol reaction: chelation controlled diastereoselective synthesis of syn -aldols
  作者：Arun K Ghosh、Jae-Hun Kim

  DOI：10.1016/s0040-4039(00)02227-9

  日期：2001.2

  A chelation controlled and highly diastereoselective synthesis of syn-aldols is described. Aldol reaction of commercially available l-phenylalaninol derived esters with a variety of bidentate oxyaldehydes proceeded with excellent syn-diastereoselectivities and isolated yields.

  描述了螯合受控且高度非对映选择性的合成顺式醇缩醛。可商购的1-苯丙的醛醇缩合反应衍生的酯与多种具有优良的二齿进行的oxyaldehydes顺-diastereoselectivities和分离收率。
• A ceric ammonium nitrate based oxidative cleavage pathway for the asymmetric aldol adducts of oxadiazinones derived from (1 R ,2 S )- N - p -methoxybenzylnorephedrine
  作者：Austin R. Leise、Nicole Comas、Doug Harrison、Dipak Patel、Eileen G. Whitemiller、Jennifer Wilson、Jacob Timms、Ian Golightly、Christopher G. Hamaker、Shawn R. Hitchcock

  DOI：10.1016/j.tetasy.2017.08.003

  日期：2017.9

  An N-4-p-methoxybenzyloxadiazinone has been prepared from (1R,2S)-norephedrine through a process of reductive amination, N-nitrosation, reduction, and cyclization. The oxadiazinone was acylated and employed in the asymmetric aldol addition reaction with aromatic and aliphatic aldehydes to yield aldol adducts in isolated yields ranging from 54% to 90%. Selected aldol adducts were treated with ceric ammonium nitrate in aqueous acetonitrile to afford the desired beta-hydroxycarboxylic acids through a tandem process of oxidative cleavage of the N-4-p-methoxybenzyl group and acidic hydrolysis of the N-3-acyl side chain. The beta-hydroxycarboxylic acids were recovered in high diastereomeric purity as determined by 500 MHz H-1 NMR spectroscopy and the absolute configuration was confirmed by polarimetry. The chiral auxiliary unit, the 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one (oxadiazinone), was converted into its corresponding 3,6-dihydro-2H-1,3,4-oxadiazin-2-one (oxadiazinone) through an oxidative pathway promoted by the ceric ammonium nitrate. (C) 2017 Elsevier Ltd. All rights reserved.
• SYNTHESIS OF OLIGOKETIDES
  申请人：Kosan Biosciences

  公开号：EP1144375A2

  公开（公告）日：2001-10-17
• [EN] SYNTHESIS OF OLIGOKETIDES<br/>[FR] SYNTHESE DE POLYCETIDES
  申请人：KOSAN BIOSCIENCES INC

  公开号：WO2000044717A2

  公开（公告）日：2000-08-03

  Facile methods for preparing diketide and triketide thioesters are disclosed. The resulting thioesters may be used as intermediates in the synthesis of desired polyketides, and may contain functional groups which ultimately reside in side chains on the resulting polyketide and thus can be used further to manipulate the polyketide so as to form derivatives. The polyketides produced may also be tailored by glycosylation, hydroxylation and the like. New polyketides and their derivatives and tailored forms are thereby produced.