(2R,4S)-3-(tert-butoxycarbonyl)-2-(tert-butyl)-4-methyloxazolidine-4-carboxylic acid | 1179522-58-7

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: (2R,4S)-3-(tert-butoxycarbonyl)-2-(tert-butyl)-4-methyloxazolidine-4-carboxylic acid
• 英文别名: (2R,4S)-2-tert-butyl-3-tert-butoxycarbonyl-4-methyl-1,3-oxazolidine-4-carboxylic acid；(2R,4S)-3-(Tert-butoxycarbonyl)-2-tert-butyl-4-methyloxazolidine-4-carboxylic acid；(2R,4S)-2-tert-butyl-4-methyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidine-4-carboxylic acid
• CAS: 1179522-58-7
• 化学式: C₁₄H₂₅NO₅
• 分子量: 287.356
• InChiKey: LDBFQVSYCCMNKF-OTYXRUKQSA-N

物化性质

• 熔点：
  117-118 °C
• 沸点：
  387.4±42.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319
• 储存条件：
  保存在2至8°C环境中，需密封并保持干燥。

反应信息

• 作为反应物：
  描述：

  (2R,4S)-3-(tert-butoxycarbonyl)-2-(tert-butyl)-4-methyloxazolidine-4-carboxylic acid 在 potassium phosphate 、 copper(l) iodide 、 草酰氯 、 三乙胺 、 N,N'-二甲基乙二胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 (2R,4S)-tert-butyl 4-((3-((2-(allyloxy)pyrimidin-4-yl)carbamoyl)-5-fluorophenyl)carbamoyl)-2-(tert-butyl)-4-methyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Synthesis of Cytimidine through a One-Pot Copper-Mediated Amidation Cascade

  摘要：

  A concise synthesis of cytimidine was developed utilizing tandem Cu-mediated N-aryl amidations followed by global deprotection. This sequence exploits a regioselective coupling of an iodobenzamide with a halopyrimidine that allows the union of three fragments in a single synthetic manipulation and will permit the efficient and rapid diversification of the cytimidine core.

  DOI：

  10.1021/ol2018196
• 作为产物：
  描述：

  (2S,4S)-3-tert-butyl 4-methyl 2-tert-butyl-4-methyl-1,3-oxazolidine-3,4-dicarboxylate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 以21.5 kg的产率得到(2R,4S)-3-(tert-butoxycarbonyl)-2-(tert-butyl)-4-methyloxazolidine-4-carboxylic acid
  参考文献：
  名称：

  Complementary Syntheses of N,O-Protected-(S)-2-methylserine on a Multikilogram Scale

  摘要：

  Two complementary and scalable approaches have been used to manufacture multikilogram quantities of N,O-protected-(S)-2-methylserine. The first approach uses a diastereomeric salt resolution of 2-methylserine methyl ester as the (1S)-(+)-camphorsulfonate salt, and was used to rapidly access 15 kg of (S)-3-tert-butoxycarbonyl-2,2,4-trimethyl-1,3-oxazolidine-4-carboxylic acid with > 99% ee. The second approach involves a stereoselective enolate methylation of a chiral cyclic L-serine derivative under cryogenic conditions. The four-step telescoped process, starting from L-serine methyl ester, was used to manufacture 20 kg of (2R,4S)-2-tert-butyl-3-tert-butoxycarbonyl-4-methyl-1,3-oxazolidine-4-carboxylic acid in 52% overall yield and 98% ee. The advantages and disadvantages for scale-up of both approaches are discussed.

  DOI：

  10.1021/op100299d

文献信息

• Total Synthesis of Nucleoside Antibiotics Plicacetin and Streptcytosine A
  作者：Jiqiang Fu、Stephane Laval、Biao Yu

  DOI：10.1021/acs.joc.8b00006

  日期：2018.7.6

  Disaccharide nucleoside antibiotics plicacetin and streptcytosine A (also named rocheicoside A) were effectively synthesized through the common precursor cytosamine. The amosamine and amicetose moieties were efficiently assembled through an α-selective O-glycosylation, and the cytosine nucleus was subsequently introduced through a β-selective gold(I)-catalyzed N-glycosylation. Further microwave-assisted

  通过普通的前体胞嘧啶有效地合成了二糖核苷抗生素plicacetin和链胞嘧啶A（也称为rocheicoside A）。通过α-选择性的O-糖基化有效地组装了阿莫胺和amic糖部分，随后通过β-选择性的金（I）催化的N-糖基化引入了胞嘧啶核。进一步的微波辅助酰胺化反应完成了模块合成。
• Visible-light-mediated decarboxylative benzoyloxylation of β-hydroxy amino acids and its application to synthesis of functional 1,2-amino alcohol derivatives
  作者：Shinsuke Inuki、Keisuke Sato、Yukari Fujimoto

  DOI：10.1016/j.tetlet.2015.09.012

  日期：2015.10

  We have developed a novel method for decarboxylative benzoyloxylation of β-hydroxy amino acids using photoredox catalyst Ru(bpy)3Cl2·6H2O and benzoylperoxide (BzO)2. This strategy was expanded to the synthesis of structurally diverse chiral 1,2-amino alcohols with different aryl or alkyl groups, starting from serine or threonine derivatives.

  我们已经开发出一种使用光氧化还原催化剂Ru（bpy）3 Cl 2 ·6H 2 O和苯甲酰过氧化物（BzO）2进行β-羟基氨基酸脱羧苯甲酰氧基化的新方法。从丝氨酸或苏氨酸衍生物开始，该策略扩展到合成具有不同芳基或烷基的结构多样的手性1,2-氨基醇。
• Total Synthesis of Nucleoside Antibiotics Amicetin, Plicacetin, and Cytosaminomycin A—D
  作者：Jiqiang Fu、Peng Xu、Biao Yu

  DOI：10.1002/cjoc.202100284

  日期：2021.10

  Amicetin and congeners constitute a small family of complex pyrimidine nucleosides, which exhibit strong antibiotic activities against Gram-positive bacteria and notably against strains of Mycobacterium tuberculosis. Herein, we report chemical synthesis of a series of disaccharide congeners of the amicetin family, including amicetin, plicacetin, and cytosaminomycin A—D. It is the first time for successful

  Amicetin 和同源物构成了一个复杂的嘧啶核苷的小家族，它们对革兰氏阳性细菌和特别是对结核分枝杆菌菌株表现出很强的抗生素活性。在此，我们报告了一系列阿米西汀家族的双糖同源物的化学合成，包括阿米西汀、普利西汀和胞质霉素 A-D。这是首次成功合成阿米西汀（原型成员）和胞质霉素。合成方法采用糖基N-苯基三氟乙酰亚胺酯和硫糖苷供体构建由 α-(1→4)-糖苷键组成的特征氨基脱氧二糖，使用金 (I)-催化N-糖基化以提供 2-脱氧-β-核苷，最后利用酰胺化和全局脱保护来完成合成。值得注意的是，发现 2-脱氧二糖供体中的 3- O-保护基团对于成功进行N-糖基化以组装胞质霉素双糖核苷至关重要。
• HEMI-FUMARATE SALT OF A 1,3,4-THIADIAZOLYL DERIVATIVE AS MODULATOR OF THE SPHINGOSINE 1-PHOSPHATE RECEPTOR
  申请人：Anson Michael Simon

  公开号：US20110034524A1

  公开（公告）日：2011-02-10

  The invention relates to the compound (2S)-2-amino-2-5-[4-(octyloxy)-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}-1-propanol hemi-fumarate, processes for its preparation, pharmaceutical compositions containing them and its use in the treatment of conditions or disorders which are mediated via the S1P1 receptor.

  本发明涉及化合物(2S)-2-氨基-2-5-[4-(辛氧基)-3-(三氟甲基)苯基]-1,3,4-噻二唑-2-基}-1-丙醇半富马酸盐、其制备方法、含有该化合物的药物组合物以及其在治疗通过S1P1受体介导的疾病或疾病中的应用。
• WO2020150385A5
  申请人：——

  公开号：WO2020150385A5

  公开（公告）日：2023-01-26