methyl (3R,5R)-5-hydroxydiazinane-3-carboxylate | 1038622-70-6

• 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 (3R,5R)-5-hydroxydiazinane-3-carboxylate
• CAS: 1038622-70-6
• 化学式: C₆H₁₂N₂O₃
• 分子量: 160.173
• InChiKey: GMPYJPLFACUDCO-RFZPGFLSSA-N

物化性质

• 沸点：
  255.8±40.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  70.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (3R,5R)-5-hydroxydiazinane-3-carboxylate 在 哌啶 、 吡啶 、 2,6-二甲基吡啶 、 2,3,5-三甲基吡啶 、 lithium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 2-trimethylsilylethyl (3R,5R)-5-[tert-butyl(dimethyl)silyl]oxy-3-[[(2S)-1-[[(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-1-oxo-1-prop-2-enoxybutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamoyl]-2-[(2S)-2-hydroxy-3-methylbutanoyl]diazinane-1-carboxylate
  参考文献：
  名称：

  Himastatin的全合成：修订后的立体结构的确认。

  摘要：

  从吡咯并吲哚啉抗-cis-1中获得了天然产物的立体异构体而不是喜伐他汀（一种具有前途的抗生素和抗肿瘤特性的不寻常的二聚二肽）。该结果导致对所提出的立体结构的修改。新的立体结构已通过总合成得到证实，其中涉及到吡咯并吲哚辛基顺式顺式1和5-羟基哌嗪酸亚单位的立体选择通道，并具有用于形成中心碳-碳键的Stille偶联。

  DOI：

  10.1002/(sici)1521-3773(19981116)37:21<2995::aid-anie2995>3.0.co;2-6
• 作为产物：
  描述：

  (R)-methyl-3-(oxiran-2-yl)propanoate 在 2,6-二甲基吡啶 、 四丁基氟化铵 、 sodium hexamethyldisilazane 、 sodium hydride 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 、 lithium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 methyl (3R,5R)-5-hydroxydiazinane-3-carboxylate
  参考文献：
  名称：

  Enantioselective synthesis of protected forms of (3R,5R)-5-hydroxypiperazic acid useful for synthesis

  摘要：

  Protected versions of (3R,SR)-5-hydroxypiperazic acid were synthesized enantioselectively in two novel ways. The first derives its chirality from D-glutamic acid while the second uses an Evans amination and a diastereoselective bromolactonization to establish the two chiral centers. Given that this amino acid is a component of several depsipeptides, these two routes enable the synthesis of multigram quantities of protected versions of 2. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01958-9

文献信息

• Total Synthesis of Himastatin: Confirmation of the Revised Stereostructure
  作者：Theodore M. Kamenecka、Samuel J. Danishefsky

  DOI：10.1002/(sici)1521-3773(19981116)37:21<2995::aid-anie2995>3.0.co;2-6

  日期：1998.11.16

  promising antibiotic and antitumor properties, was obtained from pyrroloindoline anti-cis-1. This result led to a revision of the proposed stereostructure. The new stereostructure was confirmed by the total synthesis, which involves stereoselective access to the pyrroloindoline syn-cis-1 and the 5-hydroxypiperazic acid subunit and features a Stille coupling for the formation of the central carbon-carbon bond

  从吡咯并吲哚啉抗-cis-1中获得了天然产物的立体异构体而不是喜伐他汀（一种具有前途的抗生素和抗肿瘤特性的不寻常的二聚二肽）。该结果导致对所提出的立体结构的修改。新的立体结构已通过总合成得到证实，其中涉及到吡咯并吲哚辛基顺式顺式1和5-羟基哌嗪酸亚单位的立体选择通道，并具有用于形成中心碳-碳键的Stille偶联。
• Progress toward the synthesis of piperazimycin A: exploration of the synthesis of γ-hydroxy and γ-chloropiperazic acids
  作者：J. Phillip Kennedy、John T. Brogan、Craig W. Lindsley

  DOI：10.1016/j.tetlet.2008.04.132

  日期：2008.6

  Employing Hamada's chemistry with MAOS optimization of several steps, an expedient route to key (3S,5S)- and (3R,5R)-gamma-hydroxy and (3R,5S)-gamma-chloropiperazic acids, was developed en route to a total synthesis of piperazimycin A. (C) 2008 Elsevier Ltd. All rights reserved.
• The efficient synthesis of (3R,5R)-5-hydroxypiperazic acid and its diastereomer using Lewis acid-promoted diastereoselective Strecker synthesis
  作者：Kazuishi Makino、Hang Jiang、Tatsuya Suzuki、Yasumasa Hamada

  DOI：10.1016/j.tetasy.2006.06.004

  日期：2006.7

  The stereoselective synthesis of (3R,5R)-5-hydroxypiperazic acid, a component of naturally occurring antibiotic cyclodepsipeptides, and its diastereomer was achieved via the use of Lewis acid-promoted diastereoselective Strecker synthesis as a key step, in which an interesting stereochemical reversal of diastereoselectivity by the choice of Lewis acid catalyst was observed. (c) 2006 Elsevier Ltd. All rights reserved.
• Enantioselective synthesis of protected forms of (3R,5R)-5-hydroxypiperazic acid useful for synthesis
  作者：Kristopher M. Depew、Theodore M. Kamenecka、Samuel J. Danishefsky

  DOI：10.1016/s0040-4039(99)01958-9

  日期：2000.1

  Protected versions of (3R,SR)-5-hydroxypiperazic acid were synthesized enantioselectively in two novel ways. The first derives its chirality from D-glutamic acid while the second uses an Evans amination and a diastereoselective bromolactonization to establish the two chiral centers. Given that this amino acid is a component of several depsipeptides, these two routes enable the synthesis of multigram quantities of protected versions of 2. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Discovery through Total Synthesis: A Retrospective on the Himastatin Problem
  作者：Theodore M. Kamenecka、Samuel J. Danishefsky

  DOI：10.1002/1521-3765(20010105)7:1<41::aid-chem41>3.0.co;2-d

  日期：2001.1.5

  A total synthesis of a structure proposed for himastatin was accomplished. The non-identity of the fully synthetic material with himastatin necessitated a revision of the assigned structure. Confirmation of the revised stereostructure was subsequently confirmed through total synthesis. Among the achievements during this effort were i) stereospecific routes to both anti-cis and syn-cis pyrrolindoline

  提出了针对喜伐他汀的结构的完整合成。完全合成的材料与喜伐他汀的身份不同，因此必须对指定的结构进行修改。随后通过全合成确认了修订后的立体结构的确认。在这项努力中取得的成就包括：i）抗-顺式和顺-顺式吡咯并吲哚啉亚结构的立体定向途径；ii）对映体纯形式的5-羟基哌嗪酸的实用合成；iii）形成复杂的双吲哚部分的Stille偶联，和iv）在整个正在发展的二肽域中进行有效的保护基管理。已经划定了生物药效团的轮廓。6聚体中交替的D-和L-取代基以及连接两个相同亚基的联芳基键对于维持生物活性至关重要。在另一种抗生素中模拟了这种模式，并为将来的SAR研究提供了可能的结构趋势。