octyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 446277-25-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: octyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: (3aS,4R,6S,7R,7aS)-2,2-dimethyl-6-[(2R,3R,4S,5R,6R)-6-octoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-7-phenylmethoxy-4-(phenylmethoxymethyl)-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran
• CAS: 446277-25-4
• 化学式: C₅₈H₇₂O₁₁
• 分子量: 945.203
• InChiKey: CJJHUPGORDBCAU-OXAJSGFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  69
• 可旋转键数：
  27
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  octyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 溶剂黄146 作用下， 反应 2.0h， 以98%的产率得到octyl 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
• 作为产物：
  描述：

  2,2',3,3',4',6,6'-七-O-乙酰基-alpha-D-乳糖基溴化物 在 4 A molecular sieve 、 silver perchlorate 、 sodium 、 sodium hydride 、 对甲苯磺酸 、 silver carbonate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 86.0h， 生成 octyl 2,6-di-O-benzyl-3,4-O-isopropylidene-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

文献信息

• Observations on chemical and enzymatic approaches to α-2,3-sialylated octyl β-lactoside
  作者：W.Bruce Turnbull、Jennifer A Harrison、K.P Ravindranathan Kartha、Sergio Schenkman、Robert A Field

  DOI：10.1016/s0040-4020(02)00265-x

  日期：2002.4

  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.