N-甲氧基-N-甲基-N2-{[(2-甲基-2-丙基)氧基]羰基}-L-丝氨酰胺 | 122709-20-0

• 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: N-甲氧基-N-甲基-N2-{[(2-甲基-2-丙基)氧基]羰基}-L-丝氨酰胺
• 英文名称: N-(tert-butoxycarbonyl)-L-serine N'-methoxy-N'-methylamide
• 英文别名: tert-butyl (S)-(3-hydroxy-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate；(S)-tert-butyl (3-hydroxy-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate；[2-hydroxy-1-(methoxymethylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester；Tert-butyl (S)-1-(N-methoxy-N-methylcarbamoyl)-2-hydroxyethylcarbamate；tert-butyl N-[(2S)-3-hydroxy-1-[methoxy(methyl)amino]-1-oxopropan-2-yl]carbamate
• CAS: 122709-20-0
• 化学式: C₁₀H₂₀N₂O₅
• 分子量: 248.279
• InChiKey: DJHNFMPUFGYKTR-ZETCQYMHSA-N

物化性质

• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  N-甲氧基-N-甲基-N2-{[(2-甲基-2-丙基)氧基]羰基}-L-丝氨酰胺 在 仲丁基氯化镁 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 9.0h， 生成 N-叔-丁基氧羰基-D-赤式-二氢-D-鞘氨醇
  参考文献：
  名称：

  Straightforward Synthesis of Sphinganines via a Serine-derived Weinreb Amide

  摘要：

  Sphinganines can be synthesized in just three steps from easily prepared serine-derived Weinreb amide 4. Pre-deprotonation of the acidic (N-H and O-H) protons of 4 allows for its efficient conversion to amino ketones 5. Such ketones can be selectively reduced to either erythro- or threo-sphinganines. Partially protected sphinganines 11 are also readily accessible in five steps from 4. Thus, Weinreb amide 4 represents one of the most versatile templates described to date for sphinganine synthesis.

  DOI：

  10.1021/jo030355b
• 作为产物：
  描述：

  Boc-O-苄基-L-丝氨酸-N，O-二甲基羟乙酰胺 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以73%的产率得到N-甲氧基-N-甲基-N2-{[(2-甲基-2-丙基)氧基]羰基}-L-丝氨酰胺
  参考文献：
  名称：

  Substrate-controlled crotylborationt from N-(tert-butoxycarbonyl)amino aldehydes

  摘要：

  Chiral or achiral (Z)-crotylorganoboron compounds add preferentially anti to N-(tert-butoxycarbonyl)-amino aldehydes. N-(tert-Butoxycarbonyl)prolinal 3 presents a remarkably high diastereofacial selectivity. Double stereodifferentiation, starting from compound 3, allows complete diastereoselective access to the gamma-amino-beta-hydroxy-alpha-methyl acid dolaproine 1 present in the antiproliferative dolastatin 10.

  DOI：

  10.1039/p19940001275

文献信息

• Novel Easily Recyclable Bifunctional Phosphonic Acid Carrying Tripeptides for the Stereoselective Michael Addition of Aldehydes with Nitroalkenes
  作者：Margery Cortes-Clerget、Olivier Gager、Maelle Monteil、Jean-Luc Pirat、Evelyne Migianu-Griffoni、Julia Deschamp、Marc Lecouvey

  DOI：10.1002/adsc.201500794

  日期：2016.1.7

  A novel bifunctional organocatalyst library combining both aminocatalysis and phosphonic acid activation was used for the first time as an efficient tool for the stereoselective Michael addition of aldehydes with several aromatic nitroalkenes with good selectivities up to 95:5 dr and 93:7 er. Due to their high water solubility, the catalysts were easily recyclable and could be reused over several cycles

  首次将结合了氨基催化和膦酸活化的新型双功能有机催化剂库作为有效的工具，用于醛与几种芳香族硝基烯烃的立体选择性迈克尔加成反应，选择性高达95：5 dr和93：7 er。由于它们的高水溶性，这些催化剂易于回收利用，并且可以在多个循环中重复使用，而没有任何明显的选择性损失。
• Solid-phase Total Synthesis of (−)-Apratoxin A and Its Analogues and Their Biological Evaluation
  作者：Takayuki Doi、Yoshitaka Numajiri、Takashi Takahashi、Motoki Takagi、Kazuo Shin-ya

  DOI：10.1002/asia.201000549

  日期：2011.1.3

  Two approaches for the solid‐phase total synthesis of apratoxin A and its derivatives were accomplished. In synthetic route A, the peptide was prepared by the sequential coupling of the corresponding amino acids on trityl chloride SynPhase Lanterns. After cleavage from the polymer‐support, macrolactamization of 10, followed by thiazoline formation, provided apratoxin A. This approach, however, resulted

  完成了两种方法进行固相全合成pratoxin A及其衍生物。在合成途径A中，通过在三苯甲基氯合成酶灯笼素上依次偶联相应的氨基酸来制备肽。从聚合物载体上裂解后，大环内酰胺化10，然后形成噻唑啉，提供了ApratoxinA。然而，这种方法导致收率低，因为尽管获得了类似物33，但化学选择性不足以形成噻唑啉环。但是，在合成路线B中，通过固相肽合成，使用氨基酸13 – 15和18制备了环化前体。最后的内酰胺化在溶液​​中进行以提供高总收率的人毒素A。然后，该方法成功地用于合成阿普毒素类似物。然后评估合成衍生物的细胞毒性活性。差向异构体34与Apratoxin A一样有效，O-甲基酪氨酸可以被7-叠氮基庚基酪氨酸替代而不会失去活性。在铜催化剂存在下，进行38与苯乙炔的1,3-偶极环加成反应，而不会影响噻唑啉环。
• Protein and peptide-free synthetic vaccines against streptococcus pneumoniae type 3
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：EP2851092A1

  公开（公告）日：2015-03-25

  The present invention provides a protein- and peptide-free conjugate comprising a synthetic carbohydrate and a carrier molecule, wherein the synthetic carbohydrate is a Streptococcus pneumoniae type 3 capsular polysaccharide related carbohydrate and the carrier molecule is a glycosphingolipid. Said conjugate and pharmaceutical composition thereof are useful for immunization against diseases associated with Streptococcus pneumoniae, and more specifically against diseases associated with Streptococcus pneumoniae type 3.

  本发明提供了一种不含蛋白质和多肽的缀合物，该缀合物包括一种合成碳水化合物和一个载体分子，其中合成碳水化合物是与肺炎链球菌3型荚膜多糖相关的碳水化合物，载体分子是一种糖鞘脂。所述缀合物及其药物组合物可用于免疫预防与肺炎链球菌相关的疾病，特别是与肺炎链球菌3型相关的疾病。
• [EN] PROTEIN AND PEPTIDE-FREE SYNTHETIC VACCINES AGAINST STREPTOCOCCUS PNEUMONIAE TYPE 3<br/>[FR] VACCINS SYNTHÉTIQUES SANS PROTÉINE ET SANS PEPTIDE CONTRE LE STREPTOCOCCUS PNEUMONIAE DE TYPE 3
  申请人：MAX PLANCK GES ZUR FÖRDERUNG DER WISSENSCHAFTEN E V

  公开号：WO2015040140A1

  公开（公告）日：2015-03-26

  The present invention provides a protein- and peptide-free conjugate comprising a synthetic carbohydrate and a carrier molecule, wherein the synthetic carbohydrate is a Streptococcus pneumoniae type 3 capsular polysaccharide related carbohydrate and the carrier molecule is a glycosphingolipid. Said conjugate and pharmaceutical composition thereof are useful for immunization against diseases associated with Streptococcus pneumoniae, and more specifically against diseases associated with Streptococcus pneumoniae type 3.

  本发明提供了一种不含蛋白质和多肽的缀合物，该缀合物包括一种合成碳水化合物和一个载体分子，其中合成碳水化合物是与肺炎链球菌3型荚膜多糖相关的碳水化合物，载体分子是一种糖鞘脂。所述缀合物及其药物组合物可用于免疫预防与肺炎链球菌相关的疾病，特别是与肺炎链球菌3型相关的疾病。
• Exploring Leishmania major Inositol Phosphorylceramide Synthase (LmjIPCS): Insights into the ceramide binding domain
  作者：John G. Mina、Jackie A. Mosely、Hayder Z. Ali、Paul W. Denny、Patrick G. Steel

  DOI：10.1039/c0ob00871k

  日期：——

  The synthesis of set of ceramide analogues exploring hydrophobicity in the acyl chains and the degree and nature of hydroxylation is described. These have been assayed against the parasitic protozoan enzymeLmjIPCS. These studies showed that whilst the C-3 hydroxyl group was not essential for turnover it provided enhanced affinity. Reflecting the membrane bound nature of the enzyme a long (C13) hydrocarbon ceramide tail was necessary for both high affinity and turnover. Whilst the N-acyl chain also contributed to affinity, analogues lacking the amide linkage functioned as competitive inhibitors in both enzyme and cell-based assays. A model that accounts for this observation is proposed.

  本文描述了一组神经酰胺类似物的合成，这些类似物探讨了酰基链的疏水性、羟基化的程度和性质。它们已被用于检测寄生原生动物酶LmjIPCS。这些研究表明，尽管C-3羟基团对酶的代谢转化不是必需的，但它提供了增强的亲和力。鉴于该酶的膜结合性质，需要一个长（C13）碳氢神经酰胺尾部以实现高亲和力和代谢转化。虽然N-酰基链也对亲和力有所贡献，但缺乏酰胺键连接的类似物在酶和细胞基础测试中作为竞争性抑制剂发挥了作用。针对这一观察结果，我们提出了一个理论模型。