N-Boc-O-TBS-L-allo-Thr-Gly | 308279-76-7

• 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: N-Boc-O-TBS-L-allo-Thr-Gly
• 英文别名: Boc-aThr(TBDMS)(TBDMS)-Gly-OH；2-[[(2S,3S)-3-[tert-butyl(dimethyl)silyl]oxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]acetic acid
• CAS: 308279-76-7
• 化学式: C₁₇H₃₄N₂O₆Si
• 分子量: 390.552
• InChiKey: MHPRIJAUQFITAE-AAEUAGOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-Boc-O-TBS-L-allo-Thr-Gly 在 吗啉 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 溶剂黄146 、 达卡巴嗪 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 178.5h， 生成 O-benzyl globomycin
  参考文献：
  名称：

  Globomycin 的晶体结构和全合成：相对和绝对构型的建立

  摘要：

  DOI：

  10.1021/ja002547j
• 作为产物：
  描述：

  [(2S,3S)-2-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-butyrylamino]-acetic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 N-Boc-O-TBS-L-allo-Thr-Gly
  参考文献：
  名称：

  Globomycin 的晶体结构和全合成：相对和绝对构型的建立

  摘要：

  DOI：

  10.1021/ja002547j

文献信息

• Total synthesis and NMR conformational study of signal peptidase II inhibitors, globomycin and SF-1902 A5
  作者：Toshihiro Kiho、Mizuka Nakayama、Hiroshi Kogen

  DOI：10.1016/s0040-4020(03)00110-8

  日期：2003.3

  A stereoselective total synthesis of an antibiotic, globomycin (1a), and its congener, SF-1902 A5 (1b), was achieved. Two convergent macrocyclization routes via macrolactamization or macrolactonization to form 1a are described. A conformational study by means of NMR spectroscopy was performed in several solvents. The 1H NMR spectrum of 1a indicated that the amide proton of only the l-allo-Thr residue

  立体选择性地合成了抗生素球蛋白（1a）及其同类物SF-1902 A 5（1b）。描述了通过大内酰胺化或大内酰胺化形成1a的两种会合大环化途径。在几种溶剂中通过NMR光谱进行了构象研究。1a的1 H NMR光谱表明，只有l- allo -Thr残基的酰胺质子与氢键有关。溶液相的结构不同于X射线的结构。
• Structure–activity relationships of globomycin analogues as antibiotics
  作者：Toshihiro Kiho、Mizuka Nakayama、Kayo Yasuda、Shunichi Miyakoshi、Masatoshi Inukai、Hiroshi Kogen

  DOI：10.1016/j.bmc.2003.10.055

  日期：2004.1

  Globomycin (1a), a signal peptidase II inhibitor, and its derivatives show potent antibacterial activity against Gram-negative bacteria. The synthesis and antimicrobial activity of novel globomycin analogues are reported. The hydroxyl group in the L-Ser residue was essential for the antimicrobial activity and the length of the alkyl side chain greatly influenced the activity. In addition, derivatives that had a modified cyclic core exhibited weak activity. One of the analogues showed a wider antimicrobial spectrum, effective against not only Gram-negative but also Gram-positive bacteria. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis and antimicrobial activity of novel globomycin analogues
  作者：Toshihiro Kiho、Mizuka Nakayama、Kayo Yasuda、Shunichi Miyakoshi、Masatoshi Inukai、Hiroshi Kogen

  DOI：10.1016/s0960-894x(03)00432-3

  日期：2003.7

  Globomycin, a signal peptidase II inhibitor, and its derivatives show potent antibacterial activity against Gram-negative bacteria. The synthesis and antimicrobial activity of novel globomycin analogues are reported. One of the analogues showed a more potent activity against Gram-negative bacteria than globomycin and also exhibited antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). (C) 2003 Elsevier Science Ltd. All rights reserved.
• Crystal Structure and Total Synthesis of Globomycin:  Establishment of Relative and Absolute Configurations
  作者：Hiroshi Kogen、Toshihiro Kiho、Mizuka Nakayama、Youji Furukawa、Takeshi Kinoshita、Masatoshi Inukai

  DOI：10.1021/ja002547j

  日期：2000.10.1