phenyl 4,7-di-O-acetyl-5-amino-9-O-benzyl-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 | 904895-06-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 4,7-di-O-acetyl-5-amino-9-O-benzyl-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
• 英文别名: [(1S,3R,4R,8S)-3-[(1S,2R)-1-acetyloxy-2-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-3-phenylmethoxypropyl]-6-oxo-1-phenylsulfanyl-2-oxa-5-azabicyclo[2.2.2]octan-8-yl] acetate
• CAS: 904895-06-3
• 化学式: C₅₃H₅₇NO₁₂S
• 分子量: 932.101
• InChiKey: NKCAXGOCANZWPH-RBSCJKBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  67
• 可旋转键数：
  23
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  172
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  phenyl 4,7-di-O-acetyl-5-amino-9-O-benzyl-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 在 水 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 乙腈 为溶剂， 反应 68.33h， 生成 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 (phenyl 3,5-dideoxy-2-thio-5-trifluoroacetamido-D-glycero-α-D-galacto-nonulopyranosid)onate 在 calcium sulfate 、 三氯化铝 、 二氯二茂锆 、 硼烷-三甲胺络合物 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 176.33h， 生成 phenyl 4,7-di-O-acetyl-5-amino-9-O-benzyl-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