phenyl 4,7-di-O-acetyl-9-O-benzyl-5-benzyloxycarbamoyl-3,5-dideoxy-2-thio-8-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam | 904895-07-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenyl 4,7-di-O-acetyl-9-O-benzyl-5-benzyloxycarbamoyl-3,5-dideoxy-2-thio-8-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam
• CAS: 904895-07-4
• 化学式: C₆₁H₆₃NO₁₄S
• 分子量: 1066.24
• InChiKey: KBRGSXKDAIWUAQ-DBYURNJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.78
• 重原子数：
  77.0
• 可旋转键数：
  23.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  163.82
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  phenyl 4,7-di-O-acetyl-9-O-benzyl-5-benzyloxycarbamoyl-3,5-dideoxy-2-thio-8-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam 、 碘甲烷 在 水 、 三乙胺 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.33h， 以92%的产率得到methyl [phenyl 4,7-di-O-acetyl-9-O-benzyl-5-benzyloxycarbamoyl-3,5-dideoxy-2-thio-8-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-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
• 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 calcium sulfate 、 N-碘代丁二酰亚胺 、 三氯化铝 、 三氟甲磺酸 、 硼烷-三甲胺络合物 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 sodium methylate 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 176.83h， 生成 phenyl 4,7-di-O-acetyl-9-O-benzyl-5-benzyloxycarbamoyl-3,5-dideoxy-2-thio-8-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-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