methyl (phenyl 5-acetamido-4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate | 904894-95-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (phenyl 5-acetamido-4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate
• CAS: 904894-95-7
• 化学式: C₂₉H₃₅NO₁₀S
• 分子量: 589.664
• InChiKey: CQBIXAYSYVNADY-SCVMRLTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  41.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  146.69
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl (phenyl 5-acetamido-4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate 、 2,3,4-三-O-苄基-L-吡喃岩藻糖基氟化物 在 二氯二茂锆 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 以55%的产率得到(2S,4S,5R,6R)-4-Acetoxy-6-[(1S,2R)-1-acetoxy-3-benzyloxy-2-((3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propyl]-5-acetylamino-2-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester
  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 5-acetamido-4,7-di-O-acetyl-8,9-di-O-benzylidene-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate 在 三氯化铝 、 硼烷-三甲胺络合物 、 4 A molecular sieve 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以49%的产率得到methyl (phenyl 5-acetamido-4,7-di-O-acetyl-9-O-benzyl-3,5-dideoxy-2-thio-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