(R)-3-azido-1-O-benzyl-1,2-propanediol | 131065-11-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-3-azido-1-O-benzyl-1,2-propanediol
• 英文别名: (R)-1-azido-3-benzyloxy(propan-2-ol)；(R)-1-azido-3-(benzyloxy)propan-2-ol；(2R)-1-azido-3-phenylmethoxypropan-2-ol
• CAS: 131065-11-7
• 化学式: C₁₀H₁₃N₃O₂
• 分子量: 207.232
• InChiKey: DCEXITZYUREGQB-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-3-azido-1-O-benzyl-1,2-propanediol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 生成 (2S)-2-(phenylmethoxymethyl)aziridine
  参考文献：
  名称：

  On the use of C2-symmetric aziridines as chiral auxiliaries

  摘要：

  A systematic study has been made of the utility of readily available C-2-symmetric aziridines as auxiliaries for asymmetric alkylation and aldol reactions of amide enolates. Aziridines with suitably placed oxygen atoms in the side chains proved to be useful for alkylation reactions (d.e. values up to >98%) and the results are explained in terms of an intramolecularly chelated Z-enolate species, which could be observed directly by means of NMR spectroscopy. In contrast, aziridine auxiliaries lacking side-chain oxygens performed better in aldol reactions (syn selectivity up to 98% d.e.) for which a Zimmerman-Traxler transition state is proposed. After reaction, the auxiliaries can be cleaved off nondestructively under mild conditions to afford either optically pure aldehydes or carboxylic acids.

  DOI：

  10.1016/s0040-4020(01)85546-0
• 作为产物：
  描述：

  (R)-苄氧甲基环氧乙烷 在 sodium azide 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 以85%的产率得到(R)-3-azido-1-O-benzyl-1,2-propanediol
  参考文献：
  名称：

  金催化下吡咯烷衍生物的立体选择性串联合成：(−)-Lepadiformine A 的不对称合成

  摘要：

  开发了一种 Au 催化的串联炔烃加氢胺化/亚胺离子形成/烯丙基化反应，以方便获得带有四取代碳立体中心的吡咯烷衍生物。串联反应成功地应用于 (-)-lepadiformine A（一种海洋细胞毒性三环生物碱）的 12 步不对称合成。

  DOI：

  10.1021/acs.orglett.2c02007

文献信息

• Intramolecular reductive amination strategy to the synthesis of (R)-N-Boc-2-hydroxymethylmorpholine, N-(3,4-dichlorobenzyl)(R)-2-hydroxymethylmorpholine, and (R)-2-benzylmorpholine
  作者：Rajiv T. Sawant、Suresh B. Waghmode

  DOI：10.1016/j.tet.2010.01.047

  日期：2010.3

  (R)-N-Boc-2-hydroxymethylmorpholine, N-(3,4-dichlorobenzyl)(R)-2-hydroxymethylmorpholine, and (R)-benzylmorpholine has been achieved by employing proline-catalyzed asymmetric α-aminooxylation of aldehyde and palladium-catalyzed intramolecular reductive amination of azido aldehyde as the key steps.

  通过使用脯氨酸催化，已经实现了（R）-N -Boc-2-羟甲基吗啉，N-（3,4-二氯苄基）（R）-2-羟甲基吗啉和（R）-苄基吗啉的简明高产对映选择性合成。醛的不对称α-氨氧基化和钯催化的叠氮基醛的分子内还原胺化是关键步骤。
• Synthesis and Biological Evaluation of Novel Gramicidin S Analogues
  作者：Adriaan Willem Tuin、Dimitrios Konstantinos Palachanis、Annelies Buizert、Gijsbert Marnix Grotenbreg、Emile Spalburg、Albert J. de Neeling、Roos H. Mars-Groenendijk、Daan Noort、Gijsbert A. van der Marel、Herman S. Overkleeft、Mark Overhand

  DOI：10.1002/ejoc.200900460

  日期：2009.9

  The synthesis of three new analogues of the cyclic cationic antimicrobial peptide Gramicidin S is described. These derivatives contain a modified turn region in which the DPhe-Pro motif has been replaced by a constrained furanoid sugar amino acid or a flexible linear aminoethoxy acetic acid moiety. Structural analysis revealed conformational changes in the modified turn region compared to GS. The biological

  描述了环状阳离子抗菌肽短杆菌肽 S 的三种新类似物的合成。这些衍生物含有修饰的转角区，其中 DPhe-Pro 基序已被限制性呋喃糖氨基酸或灵活的线性氨基乙氧基乙酸部分取代。结构分析揭示了与 GS 相比，修饰的转角区域的构象变化。然而，这些化合物的生物学特征类似于短杆菌肽 S 和先前描述的类似物。© 2009 Wiley-VCH Verlag GmbH & Co. KGaA，魏因海姆。
• GLS1 INHIBITORS FOR TREATING DISEASE
  申请人：Board of Regents, The University of Texas System

  公开号：US20160009704A1

  公开（公告）日：2016-01-14

  Disclosed herein are compounds and compositions useful in the treatment of GLS1 mediated diseases, such as cancer, having the structure of Formula I: Methods of inhibition GLS1 activity in a human or animal subject are also provided.

  本文揭示了一些化合物和组合物，其结构公式为I，可用于治疗GLS1介导的疾病，如癌症。还提供了抑制人类或动物主体中GLS1活性的方法。
• HETEROCYCLIC GLS1 INHIBITORS
  申请人：Board of Regents, The University of Texas System

  公开号：EP3677579A1

  公开（公告）日：2020-07-08

  Disclosed herein are compounds and compositions useful in the treatment of GLS I mediated diseases, such as cancer, having the structure of Formula I. Methods of inhibition GLS I activity in a human or animal subject are also provided.

  本文公开了用于治疗 GLS I 介导的疾病（如癌症）的具有式 I 结构的化合物和组合物。还提供了抑制人或动物体内 GLS I 活性的方法。
• Salt forms and polymorphs of (R)-1-(4-(6-(2-(4-(3,3-difluorocyclobutoxy)-6-methylpyrdin-2-yl)acetamido) pyridazin-3-yl)-2-fluorobutyl)-N-methyl-1H-1,2,3-triazole-4-carboxamide
  申请人：Board of Regents, The University of Texas System

  公开号：US10150753B2

  公开（公告）日：2018-12-11

  Disclosed herein is the compound (R)-1-(4-(6-(2-(4-(3,3-difluorocyclobutoxy)-6-methylpyridin-2-yl)acetamido)pyridazin-3-yl)-2-fluorobutyl)-N-methyl-1H-1,2,3-triazole-4-carboxamide, and salt forms and polymorphs thereof demonstrating improved exposure after oral dosing. Methods of inhibition GLS1 activity in a human or animal subject are also provided.

  本文公开了化合物(R)-1-(4-(6-(2-(4-(3,3-二氟环丁氧基)-6-甲基吡啶-2-基)乙酰氨基)哒嗪-3-基)-2-氟丁基)-N-甲基-1H-1,2,3-三唑-4-甲酰胺及其盐形式和多晶型，口服后显示出更好的暴露。还提供了抑制人或动物体内 GLS1 活性的方法。