methyl 3-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichlorethoxycarbonylamino)-β-D-glucopyranosyl]-2,4,6-tri-O-benzoyl-β-D-galactopyranoside | 1141935-29-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 3-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichlorethoxycarbonylamino)-β-D-glucopyranosyl]-2,4,6-tri-O-benzoyl-β-D-galactopyranoside
• CAS: 1141935-29-6
• 化学式: C₄₃H₄₄Cl₃NO₁₈
• 分子量: 969.177
• InChiKey: VHPYGOMXAOEWAU-KGJSGHCZSA-N

物化性质

• 沸点：
  911.7±65.0 °C(predicted)
• 密度：
  1.45±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  65.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  233.05
• 氢给体数：
  1.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  methyl 3-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichlorethoxycarbonylamino)-β-D-glucopyranosyl]-2,4,6-tri-O-benzoyl-β-D-galactopyranoside 在 甲醇 、 乙酰氯 作用下， 以77%的产率得到methyl 2,4,6-tri-O-benzoyl-3-O-[2-deoxy-2-(2,2,2-trichlorethoxycarbonylamino)-β-D-glucopyranosyl]-β-D-galactopyranoside
  参考文献：
  名称：

  The flexibility of the LeaLex Tumor Associated Antigen central fragment studied by systematic and stochastic searches as well as dynamic simulations

  摘要：

  The solution conformational behavior of the Tumor-Associated Carbohydrate Antigen Le(a)Le(x) central fragment: methyl alpha-L-fucopyranosyl-(1 -> 4)-2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1 -> 3)-beta-D-galactopyranoside was studied using three computational methods: a rigid systematic search as implemented in Sybyl, a stochastic search as implemented in MOE2004, and dynamics simulations using the SANDER module of AMBER9. Our results illustrate the complementarity of these methods to identify energetically relevant conformations and flexible linkages. In particular, the beta-GlcNAc-(1 -> 3)-Gal linkage was shown to be extremely flexible adopting a wide range of orientations around two energy minima. The modeling results were validated by comparison of theoretical distances, derived from the simulations, with experimental measurements obtained from 1D selective ROESY buildup curves on the synthetic fragment. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.020
• 作为产物：
  描述：

  methyl 2,4,6-tri-O-benzoyl-β-D-galactopyranoside 、 O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl] trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到methyl 3-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichlorethoxycarbonylamino)-β-D-glucopyranosyl]-2,4,6-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  The flexibility of the LeaLex Tumor Associated Antigen central fragment studied by systematic and stochastic searches as well as dynamic simulations

  摘要：

  The solution conformational behavior of the Tumor-Associated Carbohydrate Antigen Le(a)Le(x) central fragment: methyl alpha-L-fucopyranosyl-(1 -> 4)-2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1 -> 3)-beta-D-galactopyranoside was studied using three computational methods: a rigid systematic search as implemented in Sybyl, a stochastic search as implemented in MOE2004, and dynamics simulations using the SANDER module of AMBER9. Our results illustrate the complementarity of these methods to identify energetically relevant conformations and flexible linkages. In particular, the beta-GlcNAc-(1 -> 3)-Gal linkage was shown to be extremely flexible adopting a wide range of orientations around two energy minima. The modeling results were validated by comparison of theoretical distances, derived from the simulations, with experimental measurements obtained from 1D selective ROESY buildup curves on the synthetic fragment. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.020