methyl (phenyl 3,5-dideoxy-8,9-O-isopropylidene-2-thio-5-trifluoroacetamido-D-glycero-α-D-galacto-2-nonulopyranosid)onate | 904894-97-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (phenyl 3,5-dideoxy-8,9-O-isopropylidene-2-thio-5-trifluoroacetamido-D-glycero-α-D-galacto-2-nonulopyranosid)onate
• CAS: 904894-97-9
• 化学式: C₂₁H₂₆F₃NO₈S
• 分子量: 509.501
• InChiKey: HLSJOKMZNVXLMG-OXVLVNDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  123.55
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl (phenyl 3,5-dideoxy-8,9-O-isopropylidene-2-thio-5-trifluoroacetamido-D-glycero-α-D-galacto-2-nonulopyranosid)onate 在 silver trifluoromethanesulfonate 2,6-二甲基吡啶 、 calcium sulfate 、 二氯二茂铪 、 4 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 104.0h， 生成
  参考文献：
  名称：

  Studies on the α-(1→4)- and α-(1→8)-fucosylation of sialic acid for the total assembly of the glycan portions of complex HPG-series gangliosides

  摘要：

  A synthetic study on alpha-(1 -> 4) and alpha-(1 -> 8)-fucosylation of sialic acid is reported, with the ultimate aim being the total assembly of the glycan portion of HPG-series gangliosides. In both types of fucosylations, the combination of a phenylthio fucosyl donor and a 1,5-lactamized acceptor provided high-yielding glycosylations to afford alpha-fucosyl-sialic acid sequences. The obtained alpha-Fucp-(1 -> 8)-NeupNAc glycan having a 1,5-lactam bridge has been successfully transformed into the corresponding glycosyl donor. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.017
• 作为产物：
  描述：

  methyl (2S,4S,5R,6R)-4-acetyloxy-2-phenylsulfanyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]-5-[(2,2,2-trifluoroacetyl)amino]oxane-2-carboxylate 在 camphor-10-sulfonic acid 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 methyl (phenyl 3,5-dideoxy-8,9-O-isopropylidene-2-thio-5-trifluoroacetamido-D-glycero-α-D-galacto-2-nonulopyranosid)onate
  参考文献：
  名称：

  Studies on the α-(1→4)- and α-(1→8)-fucosylation of sialic acid for the total assembly of the glycan portions of complex HPG-series gangliosides

  摘要：

  A synthetic study on alpha-(1 -> 4) and alpha-(1 -> 8)-fucosylation of sialic acid is reported, with the ultimate aim being the total assembly of the glycan portion of HPG-series gangliosides. In both types of fucosylations, the combination of a phenylthio fucosyl donor and a 1,5-lactamized acceptor provided high-yielding glycosylations to afford alpha-fucosyl-sialic acid sequences. The obtained alpha-Fucp-(1 -> 8)-NeupNAc glycan having a 1,5-lactam bridge has been successfully transformed into the corresponding glycosyl donor. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.017