(-)-galantinic acid | 78330-63-9

• 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: (-)-galantinic acid
• 英文别名: (3S,5S,6S)-6-amino-3,5,7-trihydroxyheptanoic acid
• CAS: 78330-63-9
• 化学式: C₇H₁₅NO₅
• 分子量: 193.2
• InChiKey: ISCLAUVNBIFWBC-ZLUOBGJFSA-N

物化性质

• 熔点：
  122-126 °C
• 沸点：
  533.9±50.0 °C(Predicted)
• 密度：
  1.420±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  124
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-galantinic acid 在 盐酸 作用下， 反应 14.0h， 生成 (+)-galantinic acid 、 ((2R,4S,5S)-5-Amino-4-hydroxy-tetrahydro-pyran-2-yl)-acetic acid
  参考文献：
  名称：

  Total synthesis of galantin I. Acid-catalyzed cyclization of galantinic acid

  摘要：

  The proposed structure of galantin 1, a peptide antibiotic isolated from Bacillus pulvifaciens as a mixture of congeners (1a with the D-ornithine residue and lb with D-lysine; 1a/1b = 9/1), was shown to be incorrect by total synthesis. The substructure 3a, named galantinic acid, was an artifact, and its correct structure was assumed to be the hydroxylated form, 20a or 20b, by spectroscopic comparisons of synthetic la with natural galantin I. The synthesis of both diastereomers, 4a and 4b, again suggested that the sequence of the spermidine moiety of galantin I should be N5,N8. Finally, the correct structure of galantin I as 5a was confirmed by the synthesis of diastereomers 5a and 5b. The synthesis of 5a was accomplished in a convergent manner by the coupling of the protected forms of the constituent amino acids: D-ornithine, 6b, D-alanine, 23b, 11b, 8c, and 19a. Galantinic acid residue 20a, present in natural galantin 1, was found to undergo cyclization with retention of its C3 configuration under the chemical degradation conditions to give the artifact 3a. In order to elucidate the mode of cyclization of 20a to 3a, the synthesis of 20a and its analogues was accomplished in a stereoselective manner from D-serine. The synthesis was characterized by the stereoselective epoxidation of hydroxymethyl (Z)-allylamine 34 and alpha,beta-unsaturated delta-lactone 39. Acidolysis of 20a, 20b, and their analogues suggested that the stereoselective cyclization of galantinic acid was initiated by the formation of delta-lactone 54, which through the sequence of reactions should afford the artifact 3a.

  DOI：

  10.1021/ja00029a031
• 作为产物：
  描述：

  (E)-5-(4-methoxybenzyloxy)pent-2-en-1-ol 在 Hydroquinone 1,4-phthalazinediyl diether 、 potassium carbonate titanium(IV) isopropylate 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 四氧化锇 、 氯化亚砜 、 sodium azide 、 高氯酸 、 甲基磺酰胺 、 氢气 、 sodium acetate 、 D-(-)-酒石酸二异丙酯 、 三乙胺 、 pyridinium chlorochromate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 103.5h， 生成 (-)-galantinic acid
  参考文献：
  名称：

  （-）-没食子酸的对映选择性合成

  摘要：

  描述了一种有效的对映选择性合成（-）-没食子酸1的非蛋白原性氨基酸的方法，该方法使用Sharpless不对称环氧化，二羟基化和环状亚硫酸盐的区域选择性亲核开口作为关键步骤。

  DOI：

  10.1016/j.tetlet.2004.05.151

文献信息

• Stereoselective total synthesis of (−)-galantinic acid and 1-deoxy-5-hydroxysphingolipids via prins cyclization
  作者：Md. Ataur Rahman、Ashanul Haque、Jhillu Singh Yadav

  DOI：10.1016/j.tetlet.2020.152149

  日期：2020.7

  The stereoselective total synthesis of (−)-galantinic acid 1 and 1-deoxy-5-hydroxysphingolipids 4 is described via Prins cyclization protocol followed by reductive ring opening sequence of substituted pyrenol derivative 6. The target molecules were synthesized using a common synthetic intermediate epoxide 5. Besides, we also proposed synthetic pathways to achieve other structural analogues using common

  （ - ） -立体选择性全合成galantinic酸1和1-脱氧-5- hydroxysphingolipids 4中描述通过普林斯环化协议，随后取代pyrenol衍生物的还原性开环序列6。使用常见的合成中间体环氧化物5合成目标分子。此外，我们还提出了合成途径，以利用常见的中间体实现其他结构类似物。
• Stereoselective Total Synthesis of (-)-Galantinic Acid
  作者：Karl Gademann、Yann Bethuel

  DOI：10.1055/s-2006-941602

  日期：2006.6

  A concise, practical and stereoselective total synthesis of galantinic acid, constituent of the peptide antibiotic galantin, is reported. The title compound is obtained in six steps via Heathcock-Claisen condensation, Evans reduction and deprotection in 10% overall yield from protected serine. The route described herein thus constitutes the shortest and most efficient procedure for the preparation of the title compound disclosed so far.

  本论文报告了一种简洁、实用和立体选择性的伽兰亭酸全合成方法，伽兰亭酸是多肽抗生素伽兰亭的成分。标题化合物通过 Heathcock-Claisen 缩合、Evans 还原和脱保护等六个步骤从受保护的丝氨酸中获得，总收率为 10%。因此，本文所描述的路线是迄今为止公开的制备标题化合物的最简短、最有效的程序。
• Synthesis of (−)-galantinic acid via iterative hydrolytic kinetic resolution and tethered aminohydroxylation
  作者：Abhishek Dubey、Shruti V. Kauloorkar、Pradeep Kumar

  DOI：10.1016/j.tet.2010.02.093

  日期：2010.4

  A new synthetic strategy for (−)-galantinic acid is reported using iterative hydrolytic kinetic resolution and tethered aminohydroxylation as the key steps.

  使用迭代水解动力学拆分和束缚的氨基羟基化作为关键步骤，报道了一种新的（-）-没食子酸合成策略。
• Stereoselective Total Syntheses of Leiocarpin A and (-)-Galantinic Acid Starting­ from d-Mannitol
  作者：Kommu Nagaiah、Domalapally Sreenu、Kamaraju Purnima、Ramisetti Srinivasa Rao、Jhillu Yadav

  DOI：10.1055/s-0028-1087993

  日期：2009.4

  Stereoselective total syntheses of leiocarpin A and (-)-galantinic acid, starting from d-mannitol as a chiral synthon, are described. The key steps involve stereoselective allylations, a Grignard reaction to control the required stereogenic centers, and ring-closing metathesis followed by intramolecular Michael addition. d-mannitol - allylation - Grignard reaction - ring-closing metathesis - Michael

  描述了从d-甘露糖醇作为手性合成子开始的徕卡木霉A和（-）-没食子酸的立体选择性全部合成。关键步骤包括立体选择性烯丙基化，控制所需立体生成中心的格氏反应，以及闭环易位，随后进行分子内迈克尔加成。 d-甘露醇-烯丙基化-格氏反应-闭环复分解-迈克尔加成
• A simple entry into 1,3-diols from (R)-2,3-cyclohexylideneglyceraldehyde: synthesis of (−)-galantinic acid
  作者：Bhaskar Dhotare、Angshuman Chattopadhyay

  DOI：10.1016/j.tetasy.2009.07.030

  日期：2009.9

  Aldehydes 5, 7, and 9 derived from easily accessible (R)-2,3-cyclohexylideneglyceraldehyde 1 were used as novel substrates to obtain both syn- and anti-1,3-diols in several individual reactions by subjecting each of them to some practically viable metal-mediated Barbier-type allylations under moist conditions. In this regard, a detailed investigation was made regarding the compatibility and stereoselectivity

  醛5，7和9从容易获得（派生- [R）-2,3- cyclohexylideneglyceraldehyde 1被用作新底物，以获得这两个顺式和-抗由它们中的每经受一些在多个单独的反应-1,3-二醇在潮湿条件下几乎可行的金属介导的Barbier型烯丙基化。在这方面，对与这些醛5-7的四个这种金属介导的烯丙基化相关的相容性和立体选择性进行了详细的研究。。在几个成功的反应中具有良好的收率，具有适度的选择性，并且可以容易地色谱分离产物的非对映异构体，已成功地分离出两对对映体纯的syn -1,3和抗-1,3-二醇（6a和6b；10a和10b） ）。最后，图10b已经被利用来合成（ - ） - galantinic酸甲。