(S)-(3-methyloxetan-3-yl)methyl 2-(((benzyloxy)carbonyl)-amino)-3-hydroxypropanoate | 206191-42-6

• 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: (S)-(3-methyloxetan-3-yl)methyl 2-(((benzyloxy)carbonyl)-amino)-3-hydroxypropanoate
• 英文别名: N-benzyloxycarbonyl-L-serine 3-methyl-3-(hydroxymethyl)oxetane ester；N-[(phenylmethoxy)carbonyl]-L-serine (3-methyl-3-oxetanyl)methyl ester；(3-methyloxetan-3-yl)methyl (2S)-3-hydroxy-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 206191-42-6
• 化学式: C₁₆H₂₁NO₆
• 分子量: 323.346
• InChiKey: KRLPARCHFBDXRD-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-(3-methyloxetan-3-yl)methyl 2-(((benzyloxy)carbonyl)-amino)-3-hydroxypropanoate 在 草酰氯 、 三氟化硼乙醚 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.5h， 生成 benzyl ((1S,2S)-2-(4-(benzyloxy)phenyl)-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)propyl)carbamate
  参考文献：
  名称：

  芳基取代的 LpxC 抑制剂的合成、结构和抗生素活性

  摘要：

  锌依赖性脱乙酰酶 LpxC 催化革兰氏阴性菌中脂质 A 生物合成的关键步骤，是开发新型抗生素以对抗多重耐药革兰氏阴性菌感染的有效靶标。许多有效的 LpxC 抑制剂包含一个必不可少的苏氨酰异羟肟酸酯头基，用于与 LpxC 进行高亲和力相互作用。我们报告了新型 LpxC 抑制剂的合成、抗生素活性以及结构和酶学表征，该抑制剂在苏氨酰-异羟肟酸酯部分包含一个额外的芳基，从而扩展了 LpxC 中的抑制剂结合表面。这些化合物在酶促测定中显示出增强的 LpxC 效力和对新生弗朗西斯菌的卓越抗生素活性在细胞培养中。这些化合物对渗漏大肠杆菌菌株和野生型菌株的抗生素活性的比较揭示了强大的外膜渗透屏障的贡献，该屏障降低了化合物在细胞培养中的功效，并强调了保持平衡的疏水性和开发有效的 LpxC 靶向抗生素的亲水性特征。

  DOI：

  10.1021/jm4007774
• 作为产物：
  描述：

  3-甲基-3-羟甲基氧杂环丁烷 在 sodium iodide 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.5h， 生成 (S)-(3-methyloxetan-3-yl)methyl 2-(((benzyloxy)carbonyl)-amino)-3-hydroxypropanoate
  参考文献：
  名称：

  Synthesis of enantiomerically enriched β,γ-unsaturated-α-amino acids

  摘要：

  A variety of enantiomerically enriched beta,gamma -unsaturated-alpha -amino acids are synthesized by olefination of a Cbz-protected serine aldehyde equivalent, readily prepared from serine. A cyclic ortho ester protecting group is employed to minimize racemization. The deprotected amino acids are obtained in good yield, ranging from 70-95% ee, with double-bond geometry determined by the type of Wittig reagent used. Isotopically labeled side chains are readily introduced by this procedure, and free gamma-C-13-vinylglycine was prepared in 44% yield from the protected serine aldehyde synthon. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01146-7

文献信息

• Cysteine protease inhibitors
  申请人：——

  公开号：US20030186962A1

  公开（公告）日：2003-10-02

  of the formula (IV): 1 where: R1=R′C(O), R′SO2, R′=a bicyclic, saturated or unsaturated, 8-12 membered ring system containing 0-4 hetero atoms selected from S, O and N, which is optionally substituted with up to four substituents independently selected from groups a), b) and c) below; or R′=a monocyclic, saturated or unsaturated, 5-7 membered ring containing 0-3 hetero atoms selected from S, O and N, which monocyclic ring bears at least one substituent selected from group a) and/or c) and which may optionally bear one or two further substituents selected from group b); R4=H, C1-7-alkyl, Ar-C1-7-alkyl, Ar, C3-7-cycloalkyl; C2-7alkenyl; R3=C1-7-alkyl, C2-C7 alkenyl, C2-C7 alkenyl, C3-7-cycloalkyl, Ar-C1-7-alkyl, Ar; R5=C1-7-alkyl, halogen, Ar-C1-7-alkyl, C1-3-alkyl-CONR3R4 or a bulky amine R6 is H, C1-7-alkyl, Ar-C1-7-alkyl, C1-3-alkyl-SO2-R ix , C1-3-alkyl-C(O)—NHR ix or CH 2 XAr q is 0 or 1 have utility as inhibitors of cysteine proteases such as cathepsin K and falcipain.

  公式（IV）的翻译如下： 其中： R1=R′C(O)，R′SO2， R′=含有0-4个来自S、O和N的杂原子的8-12元环系统，可以选择饱和或不饱和的双环，可选地取代最多四个从下面的a)、b)和c)组中独立选择的取代基；或 R′=含有0-3个来自S、O和N的杂原子的5-7元环，该单环至少带有从a)组和/或c)组中选择的一个取代基，并且可选地带有从b)组中选择的一个或两个进一步的取代基； R4=H，C1-7-烷基，Ar-C1-7-烷基，Ar，C3-7-环烷基；C2-7-烯基； R3=C1-7-烷基，C2-C7烯基，C2-C7烯基，C3-7-环烷基，Ar-C1-7-烷基，Ar； R5=C1-7-烷基，卤素，Ar-C1-7-烷基，C1-3-烷基-CONR3R4或体积庞大的胺 R6为H，C1-7-烷基，Ar-C1-7-烷基，C1-3-烷基-SO2-R ix ，C1-3-烷基-C(O)—NHR ix 或CH 2 XAr q为0或1 具有作为半胱氨酸蛋白酶抑制剂的实用性，例如卡特普辛K和疟原虫蛋白酶。
• Benzothiazole derivatives with activity as adenosine receptor ligands
  申请人：——

  公开号：US20030176695A1

  公开（公告）日：2003-09-18

  The present invention relates to substituted benzothiazole derivitives and to their pharmaceutically acceptable salts useful for the treatment of diseases related to the adenosine receptor.

  本发明涉及替代苯并噻唑衍生物及其药学上可接受的盐，用于治疗与腺苷受体相关的疾病。
• ETHYNYLBENZENE DERIVATIVES
  申请人：Zhou Pei

  公开号：US20130231323A1

  公开（公告）日：2013-09-05

  Disclosed are compounds of formulae (I), (II), and (II)I: and pharmaceutically acceptable salts thereof, wherein the variables, R, R 1 , R 2 , R 3 , R 101 , L, D, Q, Y, X, and Z are defined herein. These compounds are useful for treating Gram-negative bacteria infections.

  本发明涉及式(I)、(II)和(II)I的化合物及其药学上可接受的盐，其中变量R、R1、R2、R3、R101、L、D、Q、Y、X和Z的定义如下。这些化合物可用于治疗革兰氏阴性菌感染。
• [EN] ETHYNYLBENZENE DERIVATIVES<br/>[FR] DÉRIVÉS D'ÉTHYNYLE BENZÈNE
  申请人：UNIV DUKE

  公开号：WO2012031298A3

  公开（公告）日：2012-09-27
• Stereoselective Synthesis of <i>Threo</i> and <i>Erythro</i> β-Hydroxy and β-Disubstituted-β-Hydroxy α-Amino Acids
  作者：Mark A. Blaskovich、Ghotas Evindar、Nicholas G. W. Rose、Scott Wilkinson、Yue Luo、Gilles A. Lajoie

  DOI：10.1021/jo972294l

  日期：1998.5.1

  Optically pure N-protected serine aldehyde equivalents can be prepared by the protection of the carboxylic group of serine by a cyclic ortho ester. Alkylation of N-Cbz-, N-Fmoc- or N-Boc-protected serine with oxetane tosylate 1 or bromide 2 gives the corresponding oxetane esters 4a-c which can easily be converted to the cyclic ortho esters 5a-c. A variety of unusual threo beta-hydroxy amino acids have been synthesized by Grignard addition to these optically pure serine aldehyde equivalents. The erythro diastereomers can be obtained by oxidation of the initial three adduct followed by reduction with LiBH4. Also described is a general approach for the diastereoselective synthesis of optically pure beta,beta-dialkyl-beta-hydroxy alpha-amino acids. These highly substituted amino acids are prepared by a sequence of Grignard addition to the optically active serine aldehyde equivalent, followed by oxidation of the initial adduct, and a second Grignard addition to the resulting ketone. The hydroxy adduct is obtained with very high diastereoselectivity (84-96% de). All four diastereomers can be selectively synthesized by varying the order of the Grignard additions and the chirality of the initial synthon. Removal of the protecting groups can be effected in very mild conditions, giving excellent yields of highly substituted amino acids in high diastereomeric purity.