methyl (2S,3R)-2,4-bis-(benzyloxy)-3-hydroxybutanoate | 343925-46-2

• 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: methyl (2S,3R)-2,4-bis-(benzyloxy)-3-hydroxybutanoate
• 英文别名: methyl (2S,3R)-3-hydroxy-2,4-bis(phenylmethoxy)butanoate
• CAS: 343925-46-2
• 化学式: C₁₉H₂₂O₅
• 分子量: 330.381
• InChiKey: CCHCKBBSTUWHQT-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2S,3R)-2,4-bis-(benzyloxy)-3-hydroxybutanoate 在 钯 二乙胺基三氟化硫 、 氢气 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 6.25h， 生成 methyl (2R,3S)-3-fluoro-2,4-dihydroxybutanoate
  参考文献：
  名称：

  Study on fluorination-toxicity relationships. Syntheses of 1-N-[(2R,3R)- and (2R,3S)-4-amino-3-fluoro-2-hydroxybutanoyl] derivatives of kanamycins

  摘要：

  (2R,3R)-和(2R,3S)-4-叠氮-3-氟-2-羟基丁酸(11和22)分别由3-去氧-3-氟-1,2-O-异丙叉基-a-D-古洛吡喃糖(1)和3,5-二-O-苯甲基-1,2-O-异丙叉基-a-D-木糖吡喃糖(12)制备。随后，它们被连接到适当保护的卡那霉素A或卡那霉素B类似物的H2N-1基团上，生成1-N-[(2R,3R)-和(2R,3S)-4-氨基-3-氟-2-羟基丁酰]卡那霉素(32-35)。该类化合物(32-34)表现出与卡那霉素对应1-N-[(S)-4-氨基-2-羟基丁酰](AHB)衍生物相似的抗菌活性和毒性水平。通过C-13核磁共振光谱(在D2O中，不同pD值测定)，H2N-4'''基团(32和34)的碱性强弱与对应的AHB类似物相比较低。观察到的毒性和H2N-4'''基团的碱强度之间的关系进行了讨论。

  DOI：

  10.1016/0008-6215(93)84060-j
• 作为产物：
  描述：

  3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 在 盐酸 、 sodium periodate 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 生成 methyl (2S,3R)-2,4-bis-(benzyloxy)-3-hydroxybutanoate
  参考文献：
  名称：

  Elucidation of the 2- C -methyl- d -erythritol 4-phosphate pathway for isoprenoid biosynthesis: straightforward syntheses of enantiopure 1-deoxy- d -xylulose from pentose derivatives

  摘要：

  Optically pure I-deoxy-D-xylulose, a key metabolite for feeding experiments in the methylerythritol phosphate pathway for isoprenoid biosynthesis, is conveniently synthesised from 1,2-O-isopropylidene-alpha -D-xylofuranose or from D-arabinose. This renders labelling with hydrogen isotopes possible. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00376-8

文献信息

• Elucidation of the 2- C -methyl- d -erythritol 4-phosphate pathway for isoprenoid biosynthesis: straightforward syntheses of enantiopure 1-deoxy- d -xylulose from pentose derivatives
  作者：Jean-François Hoeffler、Catherine Grosdemange-Billiard、Michel Rohmer

  DOI：10.1016/s0040-4039(01)00376-8

  日期：2001.4

  Optically pure I-deoxy-D-xylulose, a key metabolite for feeding experiments in the methylerythritol phosphate pathway for isoprenoid biosynthesis, is conveniently synthesised from 1,2-O-isopropylidene-alpha -D-xylofuranose or from D-arabinose. This renders labelling with hydrogen isotopes possible. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Study on fluorination-toxicity relationships. Syntheses of 1-N-[(2R,3R)- and (2R,3S)-4-amino-3-fluoro-2-hydroxybutanoyl] derivatives of kanamycins
  作者：Yoshiaki Takahashi、Chiga ueda、Tsutomu Tsuchiya、Yoshihiko Kobayashi

  DOI：10.1016/0008-6215(93)84060-j

  日期：1993.10

  (2R,3R)- And (2R,3S)-4-azido-3-fluoro-2-hydroxybutanoic acids (11 and 22) have been prepared from 3-deoxy-3-fluoro-1,2-0-isopropylidene-a-D-glucofuranose (1) and 3,5-di-O-benzyl-1,2-O-isopropylidene-alpha-D-xylofuranose (12), respectively. They were then coupled to the H2N-1 group of suitably protected kanamycin A or kanamycin B analogs to give, 1-N-[(2R,3R)- and (2R,3S)-4-amino-3-fluoro-2-hydroxybutanoyl]kanamycins (32-35). This group of compounds (32-34) exhibited similar antibacterial activity and toxicity level as those of the corresponding 1-N-[(S)-4-amino-2-hydroxybutanoyl] (AHB) derivatives of kanamycins. The base strength of the H2N-4''' group of 32 and 34, as determined by C-13 NMR spectroscopy (in D2O) at varying pD values, was found to be lower when compared to the basicity for the corresponding AHB analogs. The relationship between observed toxicity and base strength of the H2N-4''' group is discussed.

  (2R,3R)-和(2R,3S)-4-叠氮-3-氟-2-羟基丁酸(11和22)分别由3-去氧-3-氟-1,2-O-异丙叉基-a-D-古洛吡喃糖(1)和3,5-二-O-苯甲基-1,2-O-异丙叉基-a-D-木糖吡喃糖(12)制备。随后，它们被连接到适当保护的卡那霉素A或卡那霉素B类似物的H2N-1基团上，生成1-N-[(2R,3R)-和(2R,3S)-4-氨基-3-氟-2-羟基丁酰]卡那霉素(32-35)。该类化合物(32-34)表现出与卡那霉素对应1-N-[(S)-4-氨基-2-羟基丁酰](AHB)衍生物相似的抗菌活性和毒性水平。通过C-13核磁共振光谱(在D2O中，不同pD值测定)，H2N-4'''基团(32和34)的碱性强弱与对应的AHB类似物相比较低。观察到的毒性和H2N-4'''基团的碱强度之间的关系进行了讨论。