8-hydroxy-3,6-dioxaoctyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside | 532390-51-5

• 英文名称: 8-hydroxy-3,6-dioxaoctyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-5-acetamido-4-acetyloxy-6-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 532390-51-5
• 化学式: C₃₂H₄₉NO₂₀
• 分子量: 767.736
• InChiKey: HUTJHDJFPZDJPO-ZXVVBKGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  53
• 可旋转键数：
  26
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  263
• 氢给体数：
  2
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  8-hydroxy-3,6-dioxaoctyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside 在 sodium 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以97%的产率得到8-hydroxy-3,6-dioxaoctyl β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and potential antimetastatic activity of monovalent and divalent β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-d-glucopyranosides

  摘要：

  Anomers of monovalent and divalent beta-D-galactopyranosyl-(1-->4)-2-acetamido-2-deoxy-D-gluco-pyranosides were synthesized under different glycosylation conditions, and evaluated for in vitro antimetastatic activity. Three compounds showed promising inhibitory effects on cancer cell attachment, spreading, migration, and invasion. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00438-x
• 作为产物：
  描述：

  hexa-O-acetyl-D-lactal 在 sodium azide 、 20 % Pd(OH)2/C 、 氢气 、 一氯化碘 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 20.0 ℃ 、405.33 kPa 条件下， 反应 5.0h， 生成 8-hydroxy-3,6-dioxaoctyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of multivalent N-acetyl lactosamine modified quantum dots for the study of carbohydrate and galectin-3 interactions

  摘要：

  Ternary core/shell CdSeS/ZnS-QDs coated with N-acetyl lactosamine was prepared as a fluorescent probe to study the interactions of N-acetyl lactosamine and galectin-3. The synthesis of N-acetyl lactosamine was achieved through the 'azidoiodoglycosylation' method. The amount of ligand coated on QDs was determined by H-1 NMR and ICP-OES. The interactions between carbohydrates and galectin-3 were measured using SPR. The results revealed that the affinity of galectin-3 with di- and multivalent N-acetyl lactosamine increased 20 and 184-fold, respectively. The prepared glyco-QDs could be used as an efficient fluorescent probe to study carbohydrates and galectin-3 interactions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.035