4-amino-4-N-tert-butyloxycarbonyl-2,4,6-trideoxy-4-N,5-O-isopropylidene-2-nitro-D-galactose diethylacetal | 1421856-50-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 4-amino-4-N-tert-butyloxycarbonyl-2,4,6-trideoxy-4-N,5-O-isopropylidene-2-nitro-D-galactose diethylacetal
• 英文别名: (4R,5R)-tert-Butyl 4-((1S)-3,3-diethoxy-1-hydroxy-2-nitropropyl)-2,2,5-trimethyloxazolidine-3-carboxylate；tert-butyl (4R,5R)-4-[(1S,2R)-3,3-diethoxy-1-hydroxy-2-nitropropyl]-2,2,5-trimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 1421856-50-9
• 化学式: C₁₈H₃₄N₂O₈
• 分子量: 406.477
• InChiKey: GTKLIPOXGWNUHQ-RQJABVFESA-N

物化性质

• 沸点：
  516.1±50.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  硝基乙醛缩二乙醇 、 (4S,5R)-4-甲酰基-2,2,5-三甲基-3-恶唑烷羧酸1,1-二甲基乙基酯 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 以66.667%的产率得到
  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

文献信息

• Gram scale de novo synthesis of 2,4-diacetamido-2,4,6-trideoxy-d-galactose
  作者：Christoph Schmölzer、Christina Nowikow、Hanspeter Kählig、Walther Schmid

  DOI：10.1016/j.carres.2012.11.019

  日期：2013.2

  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.