phenyl 5-amino-3,5-dideoxy-8,9-O-isopropylidene-2-thio-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam | 904894-98-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: phenyl 5-amino-3,5-dideoxy-8,9-O-isopropylidene-2-thio-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam
• CAS: 904894-98-0
• 化学式: C₁₈H₂₃NO₆S
• 分子量: 381.45
• InChiKey: CPRZOFKMTBVIJK-VEWYWMFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.64
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  97.25
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  phenyl 5-amino-3,5-dideoxy-8,9-O-isopropylidene-2-thio-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam 、 乙酸酐 、 苯基-2,3,4-三-O-苄基-1-硫代-β-L-岩藻吡喃糖苷 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以48%的产率得到phenyl 7-O-acetyl-5-amino-3,5-dideoxy-8,9-O-isopropylidene-2-thio-4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-D-glycero-D-galacto-2-nonulopyranoside-1,5-lactam
  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 (phenyl 3,5-dideoxy-8,9-O-isopropylidene-2-thio-5-trifluoroacetamido-D-glycero-α-D-galacto-2-nonulopyranosid)onate 在 calcium sulfate 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 96.0h， 以99%的产率得到phenyl 5-amino-3,5-dideoxy-8,9-O-isopropylidene-2-thio-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam
  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