methyl (R)-3-(1'-ethoxyethoxy)-2-methylpropanoate | 910131-57-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (R)-3-(1'-ethoxyethoxy)-2-methylpropanoate
• 英文别名: methyl 3-(1-ethoxyethoxy)-(2R)-methylpropanoate；methyl (2R)-3-(1-ethoxyethoxy)-2-methylpropanoate
• CAS: 910131-57-6
• 化学式: C₉H₁₈O₄
• 分子量: 190.24
• InChiKey: ZQLOPLYIFXAYNX-GVHYBUMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (R)-3-(1'-ethoxyethoxy)-2-methylpropanoate 在 lithium aluminium tetrahydride 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 (2R)-1-(1'-ethoxyethoxy)-2-methylpentan-3-ol
  参考文献：
  名称：

  Synthesis of (2,3,1')-stegobinone, the pheromone of the drugstore beetle, with stereocontrol at C-2 and C-1'

  摘要：

  DOI：

  10.1016/s0040-4020(01)87280-x
• 作为产物：
  描述：

  (-)-甲基-D-BATA-羟基异丁酸酯 、 乙烯基乙醚 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (R)-3-(1'-ethoxyethoxy)-2-methylpropanoate
  参考文献：
  名称：

  第一次全合成抗有丝分裂化合物，（+）-phomopsidin。

  摘要：

  [反应：见正文]通过非对映选择性的跨环Diels-Alder（TADA）反应，实现了（+）-磷酸抗霉菌素的第一个全合成。合成的关键步骤包括用（-）-α-pine烯和9-BBN进行非对映选择性的炔酮还原，通过E-选择性分子内Horner-Wadsworth-Emmons（HWE）反应进行大环化，以及在Wipf条件下进行碳金属化，然后进行HWE反应在低温下选择性地构建（E）-1-甲基丙烯基和（1E，2E）-4-羧基-1,3-丁二烯基取代基。

  DOI：

  10.1021/ol036338q

文献信息

• Total synthesis of myxothiazols, novel bis-thiazole β-methoxyacrylate-based anti-fungal compounds from myxobacteria
  作者：John M. Clough、Henry Dube、Bruce J. Martin、Gerald Pattenden、K. Srinivasa Reddy、Ian R. Waldron

  DOI：10.1039/b603433k

  日期：——

  Convergent total syntheses of myxothiazols A and Z are described. The syntheses are based on elaboration of the (S)-E,E-diene thioamide 22, conversion of 22 into the bis-thiazole 27 and Wittig reactions between 27c and the aldehyde 30. The substituted beta-methoxyacrylate aldehyde 30 was produced via an Evans asymmetric aldol protocol or via the 2H-pyran-2-one 31. An E-selective Wittig reaction between

  描述了噻噻唑A和Z的收敛的总合成。合成是基于（S）-E，E-二烯硫酰胺22的制备，22转化为双噻唑27和27c与醛30之间的Wittig反应。取代的β-甲氧基丙烯酸醛30通过Evans不对称羟醛方案或通过2H-pyran-2-one31。衍生自phospho盐27c的叶立德与（+）-醛30之间的E-选择性Wittig反应导致（+）-噻唑Z（1b） ，与（+/-）-丙烯酰胺醛44的相应反应，得到（+/-）-甲噻唑A（1a）。补充研究导致了酯47b的合成，该酯对应于甲氧噻唑R和甲氧噻唑S。
• Total synthesis of the β-methoxyacrylate-based fungicide myxothiazol
  作者：Bruce J. Martin、John M. Clough、Gerald Pattenden、Ian R. Waldron

  DOI：10.1016/s0040-4039(00)60700-1

  日期：1993.8

  A total synthesis of the novel antifungal substance myxothiazol 1 isolated from the myxobacterium Myxococcus fulvus is described. The synthesis is based on elaboration of the S-E,E-diene thioamide 1 5 and the 2R S, 3S R amide aldehyde 2 5 as key intermediates, followed by conversion of 1 5 into the bis-thiazole 1 9 and a final Wittig coupling reaction between 2 5 and the salt 2 0 c leading to 7S,18S

  描述了从黄杆菌粘球菌分离的新型抗真菌物质粘噻唑1的全合成。该合成基于SE，E-二烯硫酰胺1 5和作为主要中间体的2 R S，3 S R酰胺醛2 5的精细制备，然后将1 5转化为双-噻唑1 9和最终的Wittig偶联反应之间2 5和盐2 0℃，导致7小号，18 S R，19 - [R小号myxothiazol。
• Total synthesis of tetronomycin
  作者：Kozo Hori、Naotsuka Hikage、Atsushi Inagaki、Shuho Mori、Keiichi Nomura、Eiichi Yoshii

  DOI：10.1021/jo00036a026

  日期：1992.5

  The first total synthesis of (+)-tetronomycin (1), a novel tetronic acid ionophore antibiotic, has been achieved through the synthesis and assemblage of the four cyclic segments 4, 5, 7, and 8. Construction of the C5-C-13 cyclohexyl portion 5 involves as the key step either a Beckmann fragmentation of the bicyclic ketone oxime 45 or an L-Selectride-mediated reductive annulation of the nona-2,7-dienoate 53. The C-14-C28 polyether fragment 6 was constructed by a BF3-catalyzed coupling reaction of the C-14-C22 allylsilane 7 and the C23-C28 tetrahydrofuran 8 which were derived, respectively, from L-ascorbic acid or (R)-3-hydroxyisobutyrate and L-rhamnal. The union of 5 and 6 by an aldol condensation, followed by photoisomerization of the derived diastereomeric alpha,beta-unsaturated esters, provided (Z)-61, which was converted to the aldehyde 63. Subsequent acylation of the tetronate 4 with 63 via an aldol reaction-oxidation sequence afforded the protected tetronomycin 64. Final deprotection provided synthetic tetronomycin, which was characterized as its sodium salt.
• New Nodularins: A General Method for Structure Assignment
  作者：Michio Namikoshi、Byoung Wook Choi、Ryuichi Sakai、Furong Sun、Kenneth L. Rinehart、Wayne W. Carmichael、William R. Evans、Phillip Cruz、Murray H. G. Munro、John W. Blunt

  DOI：10.1021/jo00088a014

  日期：1994.5

  A general method has been developed for assigning the structures of nodularin, a potent hepatotoxin, tumor promoter, and protein phosphatase inhibitor, and minor components isolated from a cultured and a bloom sample of the cyanobacterium Nodularia spumigena. It consists of (1) FABMS analysis (determination of molecular weight and molecular formula), (2) H-1 NMR spectroscopy on the parent compound and chiral GC analysis of an acid hydrolyzate (identification and stereochemistry of amino acid components), (3) ozonolysis followed by NaBH4 reduction (conversion to a linear peptide), and (4) FABMS/CID/MS analyses of the linear peptide and the parent compound (sequence analysis). The method has been employed in assigning structures to three new nodularins (2-4) and can be applied to other cyclic peptides containing alpha,beta-dehydroamino acid unit(s), especially the related microcystins, cyclic heptapeptide hepatotoxins. Two nodularins, [DMAdda(3)]nodularin (2) and [(6Z)-Adda(3)] nodularin (3), were obtained from a bloom sample collected from Lake Ellesmere (New Zealand), and [D-Asp(1)] nodularin (4) was isolated from cultured cells (strain L-575). The LD50s of 2 and 4 were 150 and 75 mu g/kg (ip, mice), respectively, but 3 did not show apparent toxicity at 2.0 mg/kg.