2-N-acetyl-3-O-acetyl-2,4-diamino-4-N-tert-butyloxycarbonyl-2,4,6-trideoxy-4-N,5-O-isopropylidene-D-galactose diethylacetal | 1421856-48-5

• 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: 2-N-acetyl-3-O-acetyl-2,4-diamino-4-N-tert-butyloxycarbonyl-2,4,6-trideoxy-4-N,5-O-isopropylidene-D-galactose diethylacetal
• 英文别名: tert-butyl (4S,5R)-4-[(1R,2R)-2-acetamido-1-acetyloxy-3,3-diethoxypropyl]-2,2,5-trimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 1421856-48-5
• 化学式: C₂₂H₄₀N₂O₈
• 分子量: 460.568
• InChiKey: CYQBTVOMGNXIDW-NKGKWGDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-N-acetyl-3-O-acetyl-2,4-diamino-4-N-tert-butyloxycarbonyl-2,4,6-trideoxy-4-N,5-O-isopropylidene-D-galactose diethylacetal 在 水 作用下， 反应 12.0h， 以68%的产率得到2,4-diacetamido-2,4,6-trideoxy-D-galactose diethylacetal
  参考文献：
  名称：

  Gram scale de novo synthesis of 2,4-diacetamido-2,4,6-trideoxy-d-galactose

  摘要：

  In contrast to the infection with Gram-negative bacteria, the precise mechanism of infection with their Gram-positive counterparts is still poorly understood. It has been established, that teichoic and lipoteichoic acids play an important role in host-pathogen interaction. The bacterium Streptococcus pneumoniae is one of the severe life-threatening Gram-positive pathogens and elucidation of the structure of its lipoteichoic acid revealed 2,4-diacetamido-2,4,6-trideoxy-D-galactose as a main component of the cell wall glycopolymer. Our approach toward this carbohydrate used an L-threonine derived aldehyde as starting material following the Garner protocol, which was subjected to a nitro aldol reaction with 2-nitroacetaldehyde diethylacetal to generate the galacto configurated carbon backbone. Subsequent reduction of the nitro group and peracetylation of the molecule resulted in a fully and orthogonally protected derivative, which was deprotected by a single step in pure deionized water at elevated temperatures. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.11.019
• 作为产物：
  描述：

  tert-butyl (4R,5R)-4-[(1R)-2-amino-3,3-diethoxy-1-hydroxypropyl]-2,2,5-trimethyl-1,3-oxazolidine-3-carboxylate 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以3.15 g的产率得到2-N-acetyl-3-O-acetyl-2,4-diamino-4-N-tert-butyloxycarbonyl-2,4,6-trideoxy-4-N,5-O-isopropylidene-D-galactose diethylacetal
  参考文献：
  名称：

  Gram scale de novo synthesis of 2,4-diacetamido-2,4,6-trideoxy-d-galactose

  摘要：

  In contrast to the infection with Gram-negative bacteria, the precise mechanism of infection with their Gram-positive counterparts is still poorly understood. It has been established, that teichoic and lipoteichoic acids play an important role in host-pathogen interaction. The bacterium Streptococcus pneumoniae is one of the severe life-threatening Gram-positive pathogens and elucidation of the structure of its lipoteichoic acid revealed 2,4-diacetamido-2,4,6-trideoxy-D-galactose as a main component of the cell wall glycopolymer. Our approach toward this carbohydrate used an L-threonine derived aldehyde as starting material following the Garner protocol, which was subjected to a nitro aldol reaction with 2-nitroacetaldehyde diethylacetal to generate the galacto configurated carbon backbone. Subsequent reduction of the nitro group and peracetylation of the molecule resulted in a fully and orthogonally protected derivative, which was deprotected by a single step in pure deionized water at elevated temperatures. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.11.019