H-D-Orn(Boc)-OMe | 51186-41-5

• 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: H-D-Orn(Boc)-OMe
• 英文别名: (R)-Methyl 2-amino-5-((tert-butoxycarbonyl)amino)pentanoate；methyl (2R)-2-amino-5-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS: 51186-41-5
• 化学式: C₁₁H₂₂N₂O₄
• 分子量: 246.307
• InChiKey: HCMFAYWIEPRVJR-MRVPVSSYSA-N

物化性质

• 沸点：
  349.8±32.0 °C(Predicted)
• 密度：
  1.070±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  H-D-Orn(Boc)-OMe 在 palladium on activated charcoal 二苯基膦叠氮化物 、 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 tert-butyl (4R,5S)-5-[[(4S,5R)-5-[[(2R)-1-[[(2S)-1-[[(2R)-1-methoxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]-1-oxopentan-2-yl]amino]-3-[(2-methylpropan-2-yl)oxycarbonylamino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]carbamoyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2,2-dimethyl-4-[4-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  加兰汀的全合成I.原始结构的修订

  摘要：

  提出的加兰汀I的建议结构（作为同系物的混合物（1a / 1b = 9/1）分离）在总合成中显示是不正确的，并且经过两次修订以最终在总合成中分别得到5a和5c。

  DOI：

  10.1016/s0040-4039(00)94727-0
• 作为产物：
  描述：

  N^α-Z-N^δ-Boc-D-Orn-OMe 在 palladium on activated charcoal 氢气 作用下， 反应 16.0h， 生成 H-D-Orn(Boc)-OMe
  参考文献：
  名称：

  加兰汀的全合成I.原始结构的修订

  摘要：

  提出的加兰汀I的建议结构（作为同系物的混合物（1a / 1b = 9/1）分离）在总合成中显示是不正确的，并且经过两次修订以最终在总合成中分别得到5a和5c。

  DOI：

  10.1016/s0040-4039(00)94727-0

文献信息

• Studies on the synthesis of peptides containing dehydrovaline and dehydroisoleucine based on copper-mediated enamide formation
  作者：Franziska Gille、Andreas Kirschning

  DOI：10.3762/bjoc.12.55

  日期：——

  antibiotic myxovalargin is reported. Peptide formation is based on a copper-mediated C-N cross-coupling protocol between an acyl amide and a peptidic vinyl iodide. The presence of a neighboring arginine in the vinyl iodide posed a challenge with respect to the choice of the protecting group and the reaction conditions. It was found that ornithine - a suitable precursor - is better suited than arginine for

  据报道制备了在抗生素粘多糖中存在的含有脱氢缬氨酸和脱氢异亮氨酸部分的肽片段。肽的形成基于酰基酰胺和肽基碘乙烯之间的铜介导的CN交叉偶联方案。在保护基的选择和反应条件方面，乙烯基碘中相邻精氨酸的存在提出了挑战。已发现鸟氨酸（一种合适的前体）比精氨酸更适合于实现CN交叉偶联反应的良好收率。优化的条件用于以正确的立体化学合成含有相邻鸟氨酸的肽32、33、39和40以及含有脱氢异亮氨酸的三肽44。
• [EN] SOLUTION PHASE METHOD FOR PREPARING ETELCALCETIDE<br/>[FR] PROCÉDÉ DE PRÉPARATION D'ÉTELCALCÉTIDE EN PHASE SOLUBLE
  申请人：AMGEN INC

  公开号：WO2016154580A1

  公开（公告）日：2016-09-29

  The instant disclosure is directed to solution phase fragment coupling methods for preparing etelcalcetide and its pharmaceutically acceptable salts.

  该即时披露涉及用于制备etelcalcetide及其药用可接受盐的溶液相片段偶联方法。
• Total Synthesis and Biological Evaluation of Paenilamicins from the Honey Bee Pathogen <i>Paenibacillus larvae</i>
  作者：Timur Bulatov、Sebastian Gensel、Andi Mainz、Tam Dang、Timm O. Koller、Kerstin Voigt、Julia Ebeling、Daniel N. Wilson、Elke Genersch、Roderich D. Süssmuth

  DOI：10.1021/jacs.1c09616

  日期：2022.1.12

  Paenibacillus larvae causing the lethal brood disease American Foulbrood (AFB). Here, we report the convergent total synthesis and structural revision of paenilamicin B2. Specific stereoisomers of paenilamicin B2 were synthesized for unambiguous confirmation of the natural product structure and for evaluation of biological activities. These studies revealed the N-terminal fragment of paenilamicin as an important

  类青霉素是一组复杂的聚阳离子肽次级代谢产物，具有抗菌和抗真菌活性，由破坏性蜜蜂幼虫病原体类芽孢杆菌幼虫产生，引起致命的幼虫病美洲臭虫病 (AFB)。在此，我们报道了青霉素B2的收敛全合成和结构修正。合成了青霉素 B2 的特定立体异构体，以明确确认天然产物结构并评估生物活性。这些研究揭示了青霉素的 N 末端片段是一种重要的药效基团。使用蜜蜂幼虫和昆虫病原体苏云金芽孢杆菌进行的感染试验表明，青霉霉素在蜜蜂幼虫生态位中击败了细菌竞争对手。最后，我们展示了将青霉素分类为潜在核糖体抑制剂的第一个数据。因此，我们的合成路线是了解P. larvae致病性以及在不久的将来进行彻底的结构-活性-关系以及作用模式研究的又一步。
• Total synthesis of galantin I. Acid-catalyzed cyclization of galantinic acid
  作者：Naomi Sakai、Yasufumi Ohfune

  DOI：10.1021/ja00029a031

  日期：1992.1

  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.
• Lioy, Eduardo; Kessler, Horst, Liebigs Annalen, 1996, # 2, p. 201 - 204
  作者：Lioy, Eduardo、Kessler, Horst

  DOI：——

  日期：——