(4S,5S)-3-tert-butyl 5-methyl 4-formyl-2,2-dimethyloxazolidine-3,5-dicarboxylate | 957146-87-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S,5S)-3-tert-butyl 5-methyl 4-formyl-2,2-dimethyloxazolidine-3,5-dicarboxylate
• 英文别名: 3-O-tert-butyl 5-O-methyl (4S,5S)-4-formyl-2,2-dimethyl-1,3-oxazolidine-3,5-dicarboxylate
• CAS: 957146-87-1
• 化学式: C₁₃H₂₁NO₆
• 分子量: 287.313
• InChiKey: ZRFXFFAVSLLEAM-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S,5S)-3-tert-butyl 5-methyl 4-formyl-2,2-dimethyloxazolidine-3,5-dicarboxylate 在 lithium aluminium tetrahydride 、 正丁基锂 、 偶氮二甲酸二异丙酯 、 camphor-10-sulfonic acid 、 (1-重氮基-2-氧代丙基)膦酸二甲酯 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 6.25h， 生成 (4R,5S)-tert-butyl 4-((R)-3-hydroxy-5-methylhex-1-ynyl)-5-((4-methoxybenzyloxy)-methyl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Stereoselective Synthesis of the Butyrolactone and the Oxazoline/Furan Fragment of Leupyrrin A₁

  摘要：

  Stereoselective syntheses of the Northern and the Southern fragments 2 and 3 of leupyrrin A(1) are reported. The convergent preparation of 2 is highlighted by a zirconocene-mediated one-pot cyclization-regioselective opening of an advanced diyne while the route to 3 involves a Krische allylation and a one-pot Sharpless dihydroxylation-cyclization. Comparison of the spectroscopic data with those reported for the natural product supports a relative stereochemical assignment within these heterocycles.

  DOI：

  10.1021/ol401110x
• 作为产物：
  描述：

  (4R,5S)-3-tert-butyl 5-methyl 4-((4-methoxybenzoyloxy)methyl)-2,2-dimethyloxazolidine-3,5-dicarboxylate 在 caesium carbonate 、 戴斯-马丁氧化剂 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (4S,5S)-3-tert-butyl 5-methyl 4-formyl-2,2-dimethyloxazolidine-3,5-dicarboxylate
  参考文献：
  名称：

  Stereoselective Synthesis of the Butyrolactone and the Oxazoline/Furan Fragment of Leupyrrin A₁

  摘要：

  Stereoselective syntheses of the Northern and the Southern fragments 2 and 3 of leupyrrin A(1) are reported. The convergent preparation of 2 is highlighted by a zirconocene-mediated one-pot cyclization-regioselective opening of an advanced diyne while the route to 3 involves a Krische allylation and a one-pot Sharpless dihydroxylation-cyclization. Comparison of the spectroscopic data with those reported for the natural product supports a relative stereochemical assignment within these heterocycles.

  DOI：

  10.1021/ol401110x

文献信息

• Total Synthesis of Leupyrrins A₁and B₁, Highly Potent Antifungal Agents from the Myxobacterium<i>Sorangium cellulosum</i>
  作者：Sebastian Thiede、Paul R. Wosniok、Daniel Herkommer、Thomas Debnar、Maoqun Tian、Tongtong Wang、Michael Schrempp、Dirk Menche

  DOI：10.1002/chem.201604445

  日期：2017.3.8

  involving a one‐pot lactol opening, stereoselective aldehyde addition and in situ lactonization. Furthermore, an innovative sp2‐sp3‐cross‐coupling for pyrrole functionalization and an optimized HATU‐mediated amide coupling protocol of two elaborate fragments were established. In addition, an unusual protective group strategy, involving a Teoc‐acetonide protected amine in combination with tert‐butyl

  报告了有关高产量的全合成亮丙氨酸酯酶A 1和B 1的有效策略的设计，详细说明和应用的详细信息，这是得自粘胶纤维梭菌的独特抗真菌剂。连续的锆茂介导的二炔环化和氧化锆环戊二烯中间体的区域选择性开放使简洁地进入独特的二氢呋喃片段成为可能，而丁内酯的另一种多米诺反应涉及单锅内酯开口，立体选择性醛加成和原位内酯化。此外，创新的sp 2 ‐sp 3建立了吡咯功能化的交叉偶联和两个精细片段的优化的HATU介导的酰胺偶联方案。此外，成功地制定了一种不寻常的保护基策略，其中包括由Teoc-丙酮化物保护的胺与叔丁基酯和乙酸酯的组合。这些策略和策略通常是有用的，也可用于其他功能化化合物的合成。预期通过这些总合成获得的材料将能够进一步探索这些有效的抗真菌剂的生物学特性。
• The enantioselective synthesis of APTO and AETD: polyhydroxylated β-amino acid constituents of the microsclerodermin cyclic peptides
  作者：Emily C. Shuter、Hung Duong、Craig A. Hutton、Malcolm D. McLeod

  DOI：10.1039/b707891a

  日期：——

  The polyhydroxylated beta-amino acids (2S,3R,4S,5S,7E)-3-amino-8-phenyl-2,4,5-trihydroxyoct-7-enoic acid (APTO) and (2S,3R,4S,5S,7E,9E)-3-amino-10-(4-ethoxyphenyl)-2,4,5-trihydroxydeca-7,9-dienoic acid (AETD) are key components of the microsclerodermin family of anti-fungal cyclic peptides. They have been synthesised in protected form in twelve steps using a unified strategy, with the introduction

  多羟基化的β-氨基酸（2S，3R，4S，5S，7E）-3-氨基-8-苯基-2,4,5-三羟基辛-7-烯酸（APTO）和（2S，3R，4S，5S ，7E，9E）-3-氨基-10-（4-乙氧基苯基）-2,4,5-三羟基癸-7,9-二烯酸（AETD）是抗真菌环状肽微菌皮家族的关键成分。它们已使用统一策略以十二个步骤以保护形式合成，并在合成的最后一步中从常见的醛中间体引入不饱和侧链。合成的特征是不对称氨基羟基化和二羟基化反应的有序应用，以高选择性有效地引入了靶标的立体化学。
• Discovery of Selective Nanomolar Inhibitors for Insulin-Regulated Aminopeptidase Based on α-Hydroxy-β-amino Acid Derivatives of Bestatin
  作者：Dionisios Vourloumis、Ioannis Mavridis、Alexandros Athanasoulis、Ioannis Temponeras、Despoina Koumantou、Petros Giastas、Anastasia Mpakali、Victoria Magrioti、Jacqueline Leib、Peter van Endert、Efstratios Stratikos、Athanasios Papakyriakou

  DOI：10.1021/acs.jmedchem.2c00904

  日期：2022.7.28

  The oxytocinase subfamily of M1 zinc aminopeptidases comprises emerging drug targets, including the ER-resident aminopeptidases 1 and 2 (ERAP1 and ERAP2) and insulin-regulated aminopeptidase (IRAP); however, reports on clinically relevant inhibitors are limited. Here we report a new synthetic approach of high diastereo- and regioselectivity for functionalization of the α-hydroxy-β-amino acid scaffold

  M1 锌氨肽酶的催产素酶亚家族包括新兴的药物靶点，包括 ER 驻留氨肽酶 1 和 2（ERAP1 和 ERAP2）和胰岛素调节氨肽酶（IRAP）；然而，关于临床相关抑制剂的报道有限。在这里，我们报告了一种新的合成方法，该方法具有高非对映选择性和区域选择性，可用于 bestatin 的 α-羟基-β-氨基酸支架的功能化。通过与微摩尔抑制剂复合的 ERAP1 的高分辨率 X 射线晶体结构研究了立体化学和抑制机制。通过探索 P1 侧链功能，我们获得了显着的效力和选择性，并且我们报告了一种具有细胞活性的低纳摩尔 IRAP 抑制剂，其选择性比同源酶高 120 倍以上。IRAP 与该抑制剂复合的 X 射线晶体学分析表明，与 GAMEN 环的相互作用是效力和选择性的一个未被认可的关键决定因素。总体而言，我们的结果表明，α-羟基-β-氨基酸衍生物可能构成这组氨肽酶的有用化学工具和药物先导物。
• Stereoselective Synthesis of the Butyrolactone and the Oxazoline/Furan Fragment of Leupyrrin A₁
  作者：Thomas Debnar、Tongtong Wang、Dirk Menche

  DOI：10.1021/ol401110x

  日期：2013.6.7

  Stereoselective syntheses of the Northern and the Southern fragments 2 and 3 of leupyrrin A(1) are reported. The convergent preparation of 2 is highlighted by a zirconocene-mediated one-pot cyclization-regioselective opening of an advanced diyne while the route to 3 involves a Krische allylation and a one-pot Sharpless dihydroxylation-cyclization. Comparison of the spectroscopic data with those reported for the natural product supports a relative stereochemical assignment within these heterocycles.