octyl (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyloyl-1c->4b-lactone)-(2->3)-2,6-di-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 446277-28-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: octyl (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyloyl-1c->4b-lactone)-(2->3)-2,6-di-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS: 446277-28-7
• 化学式: C₆₆H₈₃NO₁₈
• 分子量: 1178.38
• InChiKey: BVRZJAQQCRLLOI-IWNWPNABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.76
• 重原子数：
  85.0
• 可旋转键数：
  31.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  237.85
• 氢给体数：
  5.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  octyl (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyloyl-1c->4b-lactone)-(2->3)-2,6-di-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Observations on chemical and enzymatic approaches to α-2,3-sialylated octyl β-lactoside

  摘要：

  A comparison of chemical and chemo-enzymatic syntheses of alpha-2,3-sialylated octyl lactoside is reported. The chemical approach, starting from lactose and sialic acid, required 14 steps and proceeded in 5% overall yield; poor a-selectivity in the sialylation step necessitated a difficult and low yielding separation of anomers. A chemoenzymatic approach, employing recombinant Trypanosoma cruzi trans-sialidase to effect the key sialylation reaction, required 10 steps and gave a similar overall yield. Whereas the chemo-enzymatic synthesis required only three chromatographic purification steps overall, the chemical synthesis required at least nine. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00265-x
• 作为产物：
  描述：

  二甲基(6R)-5-乙酰氨基-4-O-乙酰基-3,5-二脱氧-2-硫代-6-[(1S,2R)-1,2,3-三乙酰氧基丙基]-L-苏式-己-2-酮吡喃糖苷酸酯 、 octyl 2,6-di-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 3 A molecular sieve 、 sodium methylate 作用下， 以 乙腈 、 甲醇 为溶剂， 反应 4.0h， 生成 octyl (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyloyl-1c->4b-lactone)-(2->3)-2,6-di-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 、 octyl (methyl 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosylonate)-(2->3)-2,6-di-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Observations on chemical and enzymatic approaches to α-2,3-sialylated octyl β-lactoside

  摘要：

  A comparison of chemical and chemo-enzymatic syntheses of alpha-2,3-sialylated octyl lactoside is reported. The chemical approach, starting from lactose and sialic acid, required 14 steps and proceeded in 5% overall yield; poor a-selectivity in the sialylation step necessitated a difficult and low yielding separation of anomers. A chemoenzymatic approach, employing recombinant Trypanosoma cruzi trans-sialidase to effect the key sialylation reaction, required 10 steps and gave a similar overall yield. Whereas the chemo-enzymatic synthesis required only three chromatographic purification steps overall, the chemical synthesis required at least nine. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00265-x