methyl 2,3,4-tri-O-acetyl-6,7,8,9,10-pentadeoxy-1-thio-β-L-galacto-decopyranoside | 408496-98-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-acetyl-6,7,8,9,10-pentadeoxy-1-thio-β-L-galacto-decopyranoside
• 英文别名: [(2S,3R,4R,5S,6R)-4,5-diacetyloxy-6-methylsulfanyl-2-pentyloxan-3-yl] acetate
• CAS: 408496-98-0
• 化学式: C₁₇H₂₈O₇S
• 分子量: 376.471
• InChiKey: CXDVVXABWADIPT-JZAWBGDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-6,7,8,9,10-pentadeoxy-1-thio-β-L-galacto-decopyranoside 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 2,3,4-tri-O-benzyl-6,7,8,9,10-pentadeoxy-1-thio-β-L-galacto-decopyranoside
  参考文献：
  名称：

  SYNTHESIS AND APPLICATION OF SPACER-MODIFIED L-FUCOSE ANALOGUES1

  摘要：

  Starting from 6-O-tert-butyldimethylsilyl-2,3;4,5-di-O-isopropylidenealdehydo-D-galactose (1), the carbon backbone elongated GDP-L-fucose analogue 15 bearing a chromophore tag at the end of a spacer was synthesized. Additionally, the analogues of 3-L-fucosyllactose (29) and 2'-L-fucosyllactose (36), where the fucosyl moiety is marked by a five atom alkyl chain at C-5, were prepared as labeled oligosaccharides of human milk.

  DOI：

  10.1081/car-100108277
• 作为产物：
  描述：

  三甲基甲硫基硅烷 、 1,2,3,4-tetra-O-acetyl-6,7,8,9,10-pentadeoxy-L-galacto-decopyranose 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以83%的产率得到methyl 2,3,4-tri-O-acetyl-6,7,8,9,10-pentadeoxy-1-thio-β-L-galacto-decopyranoside
  参考文献：
  名称：

  SYNTHESIS AND APPLICATION OF SPACER-MODIFIED L-FUCOSE ANALOGUES1

  摘要：

  Starting from 6-O-tert-butyldimethylsilyl-2,3;4,5-di-O-isopropylidenealdehydo-D-galactose (1), the carbon backbone elongated GDP-L-fucose analogue 15 bearing a chromophore tag at the end of a spacer was synthesized. Additionally, the analogues of 3-L-fucosyllactose (29) and 2'-L-fucosyllactose (36), where the fucosyl moiety is marked by a five atom alkyl chain at C-5, were prepared as labeled oligosaccharides of human milk.

  DOI：

  10.1081/car-100108277