tert-butyl (2S,3R)-2-[3-[[(2S)-2-amino-4-methylpentanoyl]amino]propylamino]-3-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[3-[(4-methoxyphenyl)methyl]-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]-3-hydroxypropanoate | 473710-40-6

• 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: tert-butyl (2S,3R)-2-[3-[[(2S)-2-amino-4-methylpentanoyl]amino]propylamino]-3-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[3-[(4-methoxyphenyl)methyl]-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]-3-hydroxypropanoate
• CAS: 473710-40-6
• 化学式: C₄₄H₇₇N₅O₁₀Si₂
• 分子量: 892.294
• InChiKey: BVFMGPWCJXAUNM-GWZCVPEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  61
• 可旋转键数：
  23
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  191
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,3R)-2-[3-[[(2S)-2-amino-4-methylpentanoyl]amino]propylamino]-3-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[3-[(4-methoxyphenyl)methyl]-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]-3-hydroxypropanoate 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 (2S)-2-[[(2S)-1-[[(2S)-1-[3-[[(1S,2R)-1-carboxy-2-[(2R,3S,4R,5R)-3,4-dihydroxy-5-[3-[(4-methoxyphenyl)methyl]-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]-2-hydroxyethyl]amino]propylamino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]carbamoylamino]-3-methylbutanoic acid
  参考文献：
  名称：

  Muraymycins, novel peptidoglycan biosynthesis inhibitors: synthesis and SAR of their analogues

  摘要：

  A Series Of Muraymycin analogues was synthesized. These analogues showed excellent antimicrobial activity against grain-positive organisins. These analogues also showed excellent inhibitory activity against the target peptidoglycan biosynthesis enzyme MraY, the cell membrane associated transglycosylase responsible for the formation of Lipid II. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00671-1
• 作为产物：
  描述：

  N-苄氧羰基-L-亮氨酸 在 palladium on activated charcoal 盐酸 、 氢气 、 三乙酰氧基硼氢化钠 、 1-羟基苯并三唑 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 tert-butyl (2S,3R)-2-[3-[[(2S)-2-amino-4-methylpentanoyl]amino]propylamino]-3-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[3-[(4-methoxyphenyl)methyl]-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]-3-hydroxypropanoate
  参考文献：
  名称：

  Muraymycins, novel peptidoglycan biosynthesis inhibitors: synthesis and SAR of their analogues

  摘要：

  A Series Of Muraymycin analogues was synthesized. These analogues showed excellent antimicrobial activity against grain-positive organisins. These analogues also showed excellent inhibitory activity against the target peptidoglycan biosynthesis enzyme MraY, the cell membrane associated transglycosylase responsible for the formation of Lipid II. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00671-1

文献信息

• Improved Convergent Synthesis of 5′-epi-Analogues of Muraymycin Nucleoside Antibiotics
  作者：Christian Ducho、Anatol Spork、Stefan Koppermann

  DOI：10.1055/s-0029-1217742

  日期：2009.9

  Nucleoside antibiotics represent a promising class of natural products for the development of novel antibacterial agents, with particular respect to structurally simplified analogues maintaining biological activity. There are established truncated 5'-epi-derivatives of muraymycin nucleoside antibiotics with reported antibacterial properties, but the lengthy preparation of such compounds is a major

  核苷类抗生素代表了一类有前途的天然产物，可用于开发新型抗菌剂，特别是在结构简化的类似物保持生物活性方面。已经建立了具有抗菌特性的 muraymycin 核苷抗生素的截短 5'-epi-衍生物，但此类化合物的冗长制备是更详细的构效关系 (SAR) 研究的主要障碍。本文报道了基于先前报道的使用硫叶立德化学方法对截短的 5'-epi-muraymycins 进行简明、改进的合成。这种策略的高度收敛性将允许有效合成新型 muraymycin 类似物以进行彻底的 SAR 研究。
• Muraymycins, novel peptidoglycan biosynthesis inhibitors: synthesis and SAR of their analogues
  作者：Ayako Yamashita、Emily Norton、Peter J Petersen、Beth A Rasmussen、Guy Singh、Youjin Yang、Tarek S Mansour、Douglas M Ho

  DOI：10.1016/s0960-894x(03)00671-1

  日期：2003.10

  A Series Of Muraymycin analogues was synthesized. These analogues showed excellent antimicrobial activity against grain-positive organisins. These analogues also showed excellent inhibitory activity against the target peptidoglycan biosynthesis enzyme MraY, the cell membrane associated transglycosylase responsible for the formation of Lipid II. (C) 2003 Elsevier Ltd. All rights reserved.