phenyl 4-C-azido-2,3-di-O-benzyl-4,6-dideoxy-1-thio-β-D-glucopyranoside | 369631-91-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 4-C-azido-2,3-di-O-benzyl-4,6-dideoxy-1-thio-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6S)-3-azido-2-methyl-4,5-bis(phenylmethoxy)-6-phenylsulfanyloxane
• CAS: 369631-91-4
• 化学式: C₂₆H₂₇N₃O₃S
• 分子量: 461.585
• InChiKey: CVMBZJFZNSXJLX-FRTMRTDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 4-C-azido-2,3-di-O-benzyl-4,6-dideoxy-1-thio-β-D-glucopyranoside 在 N-羟基丁二酰亚胺 、 三氟甲磺酸 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 6-O-(4-azido-2,3-di-O-benzyl-4,6-dideoxy-α-D-glucopyranosyl)-3',4'-di-O-benzyl-1-N-[(S)-4-(benzyloxycarbonylamino)-2-hydroxybutanoyl]-3,2',3'-triazidoneamine
  参考文献：
  名称：

  Tuning the Regioselectivity of the Staudinger Reaction for the Facile Synthesis of Kanamycin and Neomycin Class Antibiotics with N-1 Modification

  摘要：

  A novel method for achieving the desired regioselective reduction of the N-1 azido group on a tetraazidoneamine has been developed that leads to the synthesis of both kanamycin and neomycin class antibiotics bearing N-1 modification. Both classes of aminoglycosides are active against aminoglycoside-resistant bacteria carrying APH(3')-I and AAC(6')/APH(2").

  DOI：

  10.1021/ol051045d
• 作为产物：
  描述：

  phenyl 2,3-di-O-benzyl-1-thio-β-D-galactopyranoside 在 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 12.0h， 生成 phenyl 4-C-azido-2,3-di-O-benzyl-4,6-dideoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  胞嘧啶的正式合成——核苷类抗生素的一种成分，阿米西汀家族

  摘要：

  使用稳定的苯基硫糖苷作为关键构建块，研究了合成核苷抗生素前体阿米西汀的简便途径。

  DOI：

  10.1081/scc-100104831

文献信息

• Novel Method for the Synthesis of 3′,4′‐Dideoxygenated Pyranmycin and Kanamycin Compounds, and Studies of Their Antibacterial Activity Against Aminoglycoside‐Resistant Bacteria
  作者：Ravi Rai、Hsiao‐Nung Chen、Huiwen Chang、Cheng‐Wei Tom Chang

  DOI：10.1081/car-200059968

  日期：2005.3

  A novel protocol for converting a trans-diol to an alkene under mild conditions was developed. This method let to the synthesis of a 3',4'-dideoxykanamycin (dibekacin) analog and a 3',4'-dideoxypyranmycin that were found to be active against aminoglycoside-resistant bacteria.
• Application of Glycodiversification:  Expedient Synthesis and Antibacterial Evaluation of a Library of Kanamycin B Analogues
  作者：Jie Li、Jinhua Wang、Przemyslaw Greg Czyryca、Huiwen Chang、Thomas W. Orsak、Richard Evanson、Cheng-Wei Tom Chang

  DOI：10.1021/ol0497685

  日期：2004.4.1

  The expedient synthesis of a library of kanamycin B analogues is reported. The revealed SAR will guide future designs in developing kanamycin-type aminoglycoside antibiotics against drug-resistant bacteria.
• FORMAL SYNTHESIS OF CYTOSAMINE—A COMPONENT OF NUCLEOSIDE ANTIBIOTICS, THE AMICETIN FAMILY
  作者：Hideyuki Sugimura、Ken-ichi Watanabe

  DOI：10.1081/scc-100104831

  日期：2001.1

  A facile route to a synthetic precursor of the nucleoside antibiotics, amicetins, was investigated employing stable phenyl thioglycosides as key building blocks.

  使用稳定的苯基硫糖苷作为关键构建块，研究了合成核苷抗生素前体阿米西汀的简便途径。
• Tuning the Regioselectivity of the Staudinger Reaction for the Facile Synthesis of Kanamycin and Neomycin Class Antibiotics with N-1 Modification
  作者：Jie Li、Hsiao-Nung Chen、Huiwen Chang、Jinhua Wang、Cheng-Wei Tom Chang

  DOI：10.1021/ol051045d

  日期：2005.7.1

  A novel method for achieving the desired regioselective reduction of the N-1 azido group on a tetraazidoneamine has been developed that leads to the synthesis of both kanamycin and neomycin class antibiotics bearing N-1 modification. Both classes of aminoglycosides are active against aminoglycoside-resistant bacteria carrying APH(3')-I and AAC(6')/APH(2").