4-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate | 1366576-03-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate
• CAS: 1366576-03-5
• 化学式: C₄₃H₄₂Cl₃NO₁₇S
• 分子量: 983.228
• InChiKey: XKJUAAAOWLPQDZ-HBAVQDANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.57
• 重原子数：
  65.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  235.64
• 氢给体数：
  1.0
• 氢受体数：
  19.0

反应信息

• 作为产物：
  描述：

  phenyl 4-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-β-D-thioglucopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 3.0h， 生成 4-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl trichloroacetimidate 、 4-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  A concise chemical synthesis of a fluorescent βGal-(1,4)-S-βGlc-Cer derivative and its enzymatic elongation by glycosyltransferases

  摘要：

  A straightforward chemical synthesis of lyso-lactosylceramide with the terminal galactose linked to glucose through a beta-S-glycosidic bond is reported. The product is labeled on the amino-group with tetramethylrhodamine enabling its ultrasensitive detection in capillary electrophoresis using laser-induced fluorescence. The fluorescent product disaccharide is resistant to hydrolysis by glycosidases but is shown to remain as an acceptor substrate for glycosyltransferases for the conversion into the trisaccharides GM3 and Gb3. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.01.119