(2R)-2-{[(叔丁氧基)羰基]氨基}-3-羟丙基乙酸酯 | 503001-46-5

• 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
• 中文名称: (2R)-2-{[(叔丁氧基)羰基]氨基}-3-羟丙基乙酸酯
• 英文名称: (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-hydroxypropyl acetate
• 英文别名: (R)-(+)-3-O-acetyl-2-N-(tert-butoxycarbonyl)serinol；3-acetoxy-2-(t-butoxycarbonylamino)propan-1-ol；[(2R)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propyl] acetate
• CAS: 503001-46-5
• 化学式: C₁₀H₁₉NO₅
• 分子量: 233.265
• InChiKey: XUMANEYOPMWIJX-MRVPVSSYSA-N

物化性质

• 沸点：
  334.7±32.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R)-2-{[(叔丁氧基)羰基]氨基}-3-羟丙基乙酸酯 在 咪唑 、 氯化亚砜 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.17h， 生成 (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-[N-(prop-2'-yn-1'-yl)(4-nitrobenzene)sulfonamido]propyl acetate
  参考文献：
  名称：

  Modular, Gold-Catalyzed Approach to the Synthesis of Lead-like Piperazine Scaffolds

  摘要：

  Ring-opening of cyclic sulfamidates with propargylic sulfonamides yielded substrates for a gold-catalyzed cyclization to yield tetrahydropyrazines. Manipulation of the tetrahydropyrazines, by reduction or using multicomponent reactions, yielded piperazine scaffolds in which substitution of the carbon atoms was varied. Such scaffolds may have value in the synthesis of novel screening compounds with lead-like molecular properties.

  DOI：

  10.1021/ol402988s
• 作为产物：
  描述：

  N-Boc-丝氨醇 在 porcine pancreatic lipase 作用下， 反应 2.0h， 以98%的产率得到(2R)-2-{[(叔丁氧基)羰基]氨基}-3-羟丙基乙酸酯
  参考文献：
  名称：

  Modular, Gold-Catalyzed Approach to the Synthesis of Lead-like Piperazine Scaffolds

  摘要：

  Ring-opening of cyclic sulfamidates with propargylic sulfonamides yielded substrates for a gold-catalyzed cyclization to yield tetrahydropyrazines. Manipulation of the tetrahydropyrazines, by reduction or using multicomponent reactions, yielded piperazine scaffolds in which substitution of the carbon atoms was varied. Such scaffolds may have value in the synthesis of novel screening compounds with lead-like molecular properties.

  DOI：

  10.1021/ol402988s

文献信息

• BETA-SUBSTITUTED BETA-AMINO ACIDS AND ANALOGS AS CHEMOTHERAPEUTIC AGENTS
  申请人：QUADRIGA BIOSCIENCES, INC.

  公开号：US20150218086A1

  公开（公告）日：2015-08-06

  β-Substituted β-amino acids, β-substituted β-amino acid derivatives, and β-substituted β-amino acid analogs and (bio)isosteres and their use as chemotherapeutic agents are disclosed. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and (bio)isosteres are selective LAT1/4F2hc substrates and exhibit rapid uptake and retention in tumors expressing the LAT1/4F2hc transporter. Methods of synthesizing the β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and methods of using the compounds for treating cancer are also disclosed. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs exhibit selective uptake in tumor cells expressing the LAT1/4F2hc transporter and accumulate in cancerous cells when administered to a subject in vivo. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and (bio)isosteres exhibit cytotoxicity toward several tumor types.

  β-取代β-氨基酸，β-取代β-氨基酸衍生物，β-取代β-氨基酸类似物和（生物）同位素及其作为化疗药物的用途被披露。β-取代β-氨基酸衍生物和β-取代β-氨基酸类似物和（生物）同位素是选择性LAT1/4F2hc底物，并在表达LAT1/4F2hc转运蛋白的肿瘤中表现出快速摄取和保留。还披露了合成β-取代β-氨基酸衍生物和β-取代β-氨基酸类似物的方法以及使用这些化合物治疗癌症的方法。β-取代β-氨基酸衍生物和β-取代β-氨基酸类似物在表达LAT1/4F2hc转运蛋白的肿瘤细胞中表现出选择性摄取，并在体内给予受试者后在癌细胞中积累。β-取代β-氨基酸衍生物和β-取代β-氨基酸类似物和（生物）同位素对几种肿瘤类型表现出细胞毒性。
• Highly Efficient Synthesis of Enantiomerically Enriched 2-Hydroxymethylaziridines by Enzymatic Desymmetrization
  作者：Jun Young Choi、Richard F. Borch

  DOI：10.1021/ol062643a

  日期：2007.1.1

  Both enantiomers of protected and unprotected 2-hydroxymethylaziridines are efficiently and enantiospecifically synthesized by using a combination of enzymatic and synthetic methods. PPL was used for lipase-catalyzed desymmetrization of N-protected serinol. [reaction: see text].

  通过使用酶促方法和合成方法的组合，可以有效地和对映体特异性地合成保护的和未保护的2-羟基甲基氮丙啶的对映体。PPL用于脂肪酶催化的N保护的丝氨醇脱对称。[反应：请参见文字]。
• New Routes to Chiral Evans Auxiliaries by Enzymatic Desymmetrisation and Resolution Strategies
  作者：Claudia Neri、Jonathan M. J. Williams

  DOI：10.1002/adsc.200303006

  日期：2003.6

  synthesis using racemic auxiliaries and an enzymatic resolution. Desymmetrisation of N-Boc-protected serinol has been achieved in good yield and high enantiomeric excess using porcine pancreas lipase. This has been exploited in different ways to prepare enantiomerically enriched (4R)- and (4S)-substituted 2-oxazolidinones. In another approach to asymmetric synthesis, starting from a racemic Evans auxiliary

  本文介绍了如何通过酶促不对​​称化策略或使用外消旋助剂和酶促拆分的不对称合成方法成功制备对映体富集的伊文思助剂。使用猪胰脂肪酶已经以高收率和高对映体过量实现了N -Boc保护的丝氨醇的不对称化。已经以不同的方式利用它来制备对映体富集的（4 R）-和（4 S）-取代的2-恶唑烷酮。在另一种不对称合成方法中，从外消旋埃文斯助剂开始，通过非对映选择性醛醇缩合反应与脂肪酶催化的拆分反应，我们实现了对映体富集的β-羟基酸和对映体富集的2-恶唑烷酮的制备。
• 一种N-[(1R)-2-[1,1'-联苯]-4-基-1-(羟基甲基)乙基]氨基甲酸叔丁酯的制备方法
  申请人：山东科巢生物制药有限公司

  公开号：CN118047698A

  公开（公告）日：2024-05-17

  本发明提供了一种抗心衰新药沙库巴曲缬沙坦钠关键中间体N‑[(1R)‑2‑[1,1'‑联苯]‑4‑基‑1‑(羟基甲基)乙基]氨基甲酸叔丁酯的制备方法，包括以2‑氨基‑1,3‑丙二醇Boc衍生物化合物1为起始原料，经固化酶催化的酯化反应、环合反应、氧化反应，开环反应，最后水解得到目标产物化合物7；该方法路线短，效率高，起始原料价格便宜，反应过程中避免了使用昂贵手性催化剂，大大降低了工艺成本，整个工艺实验条件要求低，操作简单，收率高，适合工艺放大。#imgabs0#
• Preparation of 2-oxazolidinones by enzymatic desymmetrisation
  作者：Claudia Neri、Jonathan M.J. Williams

  DOI：10.1016/s0957-4166(02)00547-5

  日期：2002.10

  Desymmetrisation of achiral N-Boc-serinol was achieved through enzymatic acetylation. Further transformation provided oxazolidinones with >98% enantiomeric excess. (C) 2002 Elsevier Science Ltd. All rights reserved.