ethyl 2,4-diacetamido-2,4,6-trideoxy-α-D-galactopyranoside | 1421856-53-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,4-diacetamido-2,4,6-trideoxy-α-D-galactopyranoside
• CAS: 1421856-53-2
• 化学式: C₁₂H₂₂N₂O₅
• 分子量: 274.317
• InChiKey: WWPNTHJLSAFEAM-JJDXKYNWSA-N

反应信息

• 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 在 吡啶 、 4-二甲氨基吡啶 、 水 作用下， 反应 12.0h， 生成 2,4-diacetamido-2,4,6-trideoxy-α-D-galactopyranose 、 2,4-diacetamido-2,4,6-trideoxy-β-D-galactopyranose 、 ethyl 2,4-diacetamido-2,4,6-trideoxy-α-D-galactopyranoside
  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