methyl 3(R)-<<(1,1-dimethylethoxy)carbonyl>amino>-5-methylhexanoate | 116263-98-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 3(R)-<<(1,1-dimethylethoxy)carbonyl>amino>-5-methylhexanoate
• 英文别名: (R)-3-tert-butoxycarbonylamino-5-methylhexanoic acid methyl ester；methyl 3(R)-{[(1,1-dimethylethoxy)carbonyl]amino}-5-methylhexanoate；methyl (3R)-5-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
• CAS: 116263-98-0
• 化学式: C₁₃H₂₅NO₄
• 分子量: 259.346
• InChiKey: YACSTGFJEALEJV-SNVBAGLBSA-N

物化性质

• 沸点：
  345.3±25.0 °C(Predicted)
• 密度：
  0.998±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3(R)-<<(1,1-dimethylethoxy)carbonyl>amino>-5-methylhexanoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 吡啶 、 盐酸 、 lithium hydroxide 、 氢氟酸 、 双氧水 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 16.75h， 生成 (Z)-(2R,3S,6R,8R)-8-(9H-Fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2,10-dimethyl-undec-4-enoic acid
  参考文献：
  名称：

  广泛地立体多样化的支架，用于面向多样性的文库合成。

  摘要：

  报告了12和19的立体多样性库的合成，其中每个星号代表一个独立变化的立体中心。这些支架为研究文库合成中的几何多样性提供了额外的模板。这些N-Fmoc-氨基酸的文库通过掺入肽序列进一步功能化，证明了12和19作为多样性导向合成的基础材料的实用性。

  DOI：

  10.1021/ol027116f
• 作为产物：
  描述：

  BOC-D-亮氨酸 在 N-甲基吗啉 、 silver benzoate 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 2.08h， 生成 methyl 3(R)-<<(1,1-dimethylethoxy)carbonyl>amino>-5-methylhexanoate
  参考文献：
  名称：

  广泛地立体多样化的支架，用于面向多样性的文库合成。

  摘要：

  报告了12和19的立体多样性库的合成，其中每个星号代表一个独立变化的立体中心。这些支架为研究文库合成中的几何多样性提供了额外的模板。这些N-Fmoc-氨基酸的文库通过掺入肽序列进一步功能化，证明了12和19作为多样性导向合成的基础材料的实用性。

  DOI：

  10.1021/ol027116f

文献信息

• Lewis Acid−Lewis Acid Heterobimetallic Cooperative Catalysis:  Mechanistic Studies and Application in Enantioselective Aza-Michael Reaction
  作者：Noriyuki Yamagiwa、Hongbo Qin、Shigeki Matsunaga、Masakatsu Shibasaki

  DOI：10.1021/ja054066b

  日期：2005.9.28

  3-3 mol % with enones. To broaden the substrate scope of the reaction to carboxylic acid derivatives, alpha,beta-unsaturated N-acylpyrroles were used as monodentate, carboxylic acid derivatives. With beta-alkyl-substituted N-acylpyrroles, the reaction proceeded smoothly and the products were obtained in high yield and good ee. Transformation of the 1,4-adducts from enones and alpha,beta-unsaturated N-acylpyrroles

  描述了由稀土-碱金属异双金属配合物促进的甲氧基胺催化不对称氮杂-迈克尔反应的全部细节，证明了路易斯酸-路易斯酸协同催化的有效性。首先，使用烯酮作为底物，以良好的产率 (57-98%) 和高 ee (81-96%) 获得 1,4-加合物。使用烯酮成功地将催化剂负载降低到 0.3-3 mol%。为了将反应的底物范围扩大到羧酸衍生物，α，β-不饱和 N-酰基吡咯被用作单齿羧酸衍生物。使用β-烷基取代的N-酰基吡咯，反应顺利进行，产物收率高，ee值好。来自烯酮和α的1,4-加合物的转化，β-不饱和N-酰基吡咯得到相应的手性氮丙啶和β-氨基酸。还描述了详细的机械研究，包括动力学、核磁共振分析、非线性效应和稀土金属效应。详细讨论了路易斯酸-路易斯酸协同机制，包括底物配位模式。
• Design of novel inhibitors of aminopeptidases. Synthesis of peptide-derived diamino thiols and sulfur replacement analogs of bestatin
  作者：E. M. Gordon、J. D. Godfrey、N. G. Delaney、M. M. Asaad、D. Von Langen、D. W. Cushman

  DOI：10.1021/jm00119a023

  日期：1988.11

  Investigations were directed toward inhibition of an aminopeptidase, isolated from rat brain, which has been implicated in the metabolic inactivation of enkephalins. The design rationale and synthesis of novel peptidyl diamino thiol inhibitors of rat brain aminopeptidase are presented, along with accompanying structure-activity analysis. Some of the reported compounds are highly active aminopeptidase inhibitors and possess enzyme inhibitory potency in the nanomolar range (62; I50 = 1 nM). Analysis of the data permits speculations on possible modes of binding of diamino thiols to aminopeptidase. Other investigations were directed toward understanding the mode of enzyme binding of the naturally occurring aminopeptidase inhibitor bestatin. On the basis of published models of enzyme binding, replacement of the C-2 hydroxyl group of bestatin by a sulfhydryl group was anticipated to lead to enhanced inhibition due to a strengthened interaction of this group with enzymic zinc. Contrary to expectations, "thiobestatin" inhibited rat brain aminopeptidase with only the same degree of effectiveness as the corresponding alcohol. Speculations on the possible mode of enzyme-inhibitor binding of bestatin are offered.
• CD Spectra in Methanol ofβ-Oligopeptides Consisting ofβ-Amino Acids with Functionalized Side Chains, with Alternating Configuration, and with Geminal Backbone Substituents - Fingerprints of New Secondary Structures?
  作者：Dieter Seebach、Thierry Sifferlen、Pascal A. Mathieu、Andreas M. Häne、Christoph M. Krell、Daniel J. Bierbaum、Stefan Abele

  DOI：10.1002/1522-2675(20001108)83:11<2849::aid-hlca2849>3.0.co;2-r

  日期：2000.11.8

  beta -Hexa-, beta -hepta-, and beta -nonapeptides, 1-6, which carry functionalized side chains (CO(2)R, CO(2)(-), (CH(2))(4)NH(3)(+), CH(2)-CH=CH(2)) consisting of beta (3)-amino-acid residues of alternating configuration, or which carry geminal substituents in the 2- or 3-positions of all residues, have been synthesized (Schemes 1 - 3), and their CD spectra in MeOH are reported (Figs. 2 - 6). Strong Cotton effects (Theta >10(5)) are indicative of the presence of chiral secondary structures. It is suggested by simple modelling (Fig. 1) that the new beta -peptides should not be able to fold to the familiar 3(14)-helical structures. Still, three of them (3, 4, and 5) give rise to CD spectra matching those of beta -peptides that are known to be present as (M)- or (P)3(14)-helices in MeOH solution. While possible folding motifs (Figs. 3, b, and 7) of the new beta -peptides have been identified in crystal structures, an interpretation of the CD spectra has to be postponed until NMR solution structures become available. A list of all beta -peptides giving rise to CD spectra with a minimum near 215 nm is included (Table).
• GORDON, E. M.;GODFREY, J. D.;DELANEY, N. G.;ASAAD, M. M.;VON, LANGEN D.;C+, J. MED. CHEM., 31,(1988) N 11, C. 2199-2211
  作者：GORDON, E. M.、GODFREY, J. D.、DELANEY, N. G.、ASAAD, M. M.、VON, LANGEN D.、C+

  DOI：——

  日期：——