(2R,3R,4R)-2,4,6-trimethyl-3-hydroxyheptanoic acid | 474095-61-9

• 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: (2R,3R,4R)-2,4,6-trimethyl-3-hydroxyheptanoic acid
• 英文别名: (2R,3R,4R)-3-hydroxy-2,4,6-trimethylheptanoic acid
• CAS: 474095-61-9
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: GAILTKKTRDYYQA-IWSPIJDZSA-N

物化性质

• 沸点：
  298.9±23.0 °C(Predicted)
• 密度：
  1.005±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  (2R,3R,4R)-2,4,6-trimethyl-3-hydroxyheptanoic acid 在 锂硼氢 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (4R,5S)-4-[(1R)-1,3-dimethylbutyl]-2,2,5-trimethyl-1,3-dioxane
  参考文献：
  名称：

  Stereoselective synthesis of (2R,3R,4R)-3-hydroxy-2,4,6-trimethylheptanoic acid and determination of the absolute stereochemistry of the natural product from callipeltin A

  摘要：

  A revised stereostructure of 3-hydroxy-2,4,6-trimethylheptanoic acid, the beta-hydroxy acid that acylates the N-terminus of callipeltin A. is proposed on the basis of analysis of J-coupling in the H-1 NMR spectrum of the acetonide derivative obtained front the acid hydrolysate of callipeltin A. The proposed Structure was definitively confirmed by enantioselective synthesis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00328-2
• 作为产物：
  描述：

  (R)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4-trimethylpentanamide 在 palladium on activated charcoal sodium hypochlorite 、 sodium periodate 、 四氧化锇 、 lithium aluminium tetrahydride 、 甲酸 、 三氟甲磺酸 、 三氟化硼乙醚 、 氨基磺酸 、 氢气 、 乙酸乙酯 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 正己烷 、 二氯甲烷 、 环己烷 为溶剂， -78.0~20.0 ℃ 、303.98 kPa 条件下， 反应 18.5h， 生成 (2R,3R,4R)-2,4,6-trimethyl-3-hydroxyheptanoic acid
  参考文献：
  名称：

  Asymmetric Synthesis of Four Diastereomers of 3-Hydroxy-2,4,6-trimethylheptanoic Acid:  Proof of Configurational Assignment

  摘要：

  Four unique diastereomers of 3-hydroxy-2,4,6-trimethylheptanoic acid-(2R,3R,4R), (2S,3R,4R), (2S,3R,4S), and (2R,3R,4S)-the fatty acid component of callipeltin A and D, have been synthesized from commercially available (+)- and (-)-pseudoephedrine propionamide in 6 steps and 59% average overall yield. Comparison of the H-1 and C-13 NMR and optical rotation data of the resulting isomers with the natural fragment unambiguously verifies the configurational assignment of the natural isomer as (2R,3R,4R).

  DOI：

  10.1021/jo034738l

文献信息

• Synthetic Studies on Callipeltin A: Stereoselective Synthesis of (2R,3R,4S)-3-Hydroxy-2,4,6-trimethylheptanoic Acid
  作者：Gowravaram Sabitha、K. Yadagiri、G. Chandrashekhar、J. Yadav

  DOI：10.1055/s-0030-1258315

  日期：2010.12

  Asymmetric synthesis of (2R,3R,4S)-3-hydroxy-2,4,6-trimethylheptanoic acid, the β-hydroxy acid unit that acylates the N-terminus of cyclic depsipeptide callipeltin A, has been devised. The approach involves the desymmetrization of a bicyclic precursor, which generates the three chiral centers. asymmetric synthesis - callipeltin A - desymmetrization - natural products

  已经设计了（2 R，3 R，4 S）-3-羟基-2,4,6-三甲基庚酸的不对称合成，所述β-羟基酸单元酰化了环二肽肽callipeltin A的N-末端。该方法涉及双环前体的去对称化，其产生三个手性中心。 不对称合成-卡培普尔汀A-去对称化-天然产物
• Preparation of (2 R , 3 R , 4 R )-3-hydroxy-2,4,6-trimethylheptanoic acid via enzymatic desymmertization
  作者：Yoshinori Tokairin、Hiroyuki Konno

  DOI：10.1016/j.tet.2016.11.050

  日期：2017.1

  Synthesis of a unique fatty acyl unit to build the N-terminus of callipeltin A and homophymine B is described. Our approach to, access (2R, 3R, 4R)-3-hydroxy-2,4,6-trimethylheptanoic acid uses enzymatic hydrolysis for the desymmetrization of achiral acetate, followed by diastereoselective Roush crotylboration and Wittig olefination for the backbone construction. (C) 2016 Elsevier Ltd. All rights reserved.
• Complete Stereochemistry of Neamphamide A and Absolute Configuration of the β-Methoxytyrosine Residue in Papuamide B
  作者：Naoya Oku、Ravi Krishnamoorthy、Alan G. Benson、Robert L. Ferguson、Mark A. Lipton、Lawrence R. Phillips、Kirk R. Gustafson、James B. McMahon

  DOI：10.1021/jo0508853

  日期：2005.8.1

  [GRAPHICS]The absolute stereochemistry of the three unresolved structural components in neamphamide A (1) was determined to be (R)-beta-methoxy-L-tyrosine, (2R,3R,4S)-4-amino-7-guanidino-2,3-dihydroxyheptanoic acid, and (2R,3R,4R)-3-hydroxy-2,4,6-trimethylheptanoic acid. Stereochemical assignments were made by chemical degradation of 1, derivatization of the resulting products, and then spectroscopic and chromatographic comparison of the derivatives with synthetically prepared standards. Using the same analytical protocol developed for 1, the beta-methoxytyrosine residue in papuamide B (2) was found to be (R)-beta-methoxy-D-tyrosine. This represents a rare example of divergent stereochemistry in an unusual amino acid residue that is present in two closely related classes of peptides.
• [EN] SYNTHETIC PROCESS FOR THE MANUFACTURE OF PIPECOLIDEPSIN COMPOUNDS<br/>[FR] PROCÉDÉ DE SYNTHÈSE POUR LA FABRICATION DE COMPOSÉS DE PIPÉCOLIDEPSINE
  申请人：PHARMA MAR SA

  公开号：WO2014108526A1

  公开（公告）日：2014-07-17

  (I) wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, n and Y are as described. The invention provides a process for the synthesis of complex pipecolidepsin and related compounds of formula (I), opening a new field of compounds with useful biological properties. The invention also provides intermediates, useful in the synthesis of compounds of formula (I).