4-pentenyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside | 893554-71-7

• 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: 4-pentenyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside
• CAS: 893554-71-7
• 化学式: C₃₂H₃₈O₆
• 分子量: 518.65
• InChiKey: UXTNZMFJGCLKSI-UNKWROQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  38.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-pentenyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside 在 氨 、 silver trifluoromethanesulfonate 、 sodium 作用下， 以 乙二醇二甲醚 、 乙醚 为溶剂， 反应 2.75h， 生成 (2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-pent-4-enoxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
  参考文献：
  名称：

  Syntheses and Vero toxin-binding activities of carbosilane dendrimers periphery-functionalized with galabiose

  摘要：

  Carbosilane dendrimers bearing galabiose (Gal alpha 1-4Gal) with three, four, and six galabiose units at the periphery of the dendrimers were synthesized for use as artificial inhibitors against Shiga toxins (Stxs) produced by Escherichia coli O157:H7. The galabiose unit, prepared from penta-O-acetyl-beta-D-galactopyranose, was linked with carbosilane dendrimers of three shapes to afford acety I-protected glycodendrimers in good yields. De-O-acetylation of the clusters was carried out in the presence of NaOMe and then aq NaOH to give the desired three shapes of galabiose-coated carbosilane dendrimers. Their biological activities toward Stxs were evaluated by kinetic analysis, binding assays, and cytotoxic assays. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.042
• 作为产物：
  描述：

  4-pentenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside 在 三氯化铝 、 trimethylamine borane 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以90%的产率得到4-pentenyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Syntheses and Vero toxin-binding activities of carbosilane dendrimers periphery-functionalized with galabiose

  摘要：

  Carbosilane dendrimers bearing galabiose (Gal alpha 1-4Gal) with three, four, and six galabiose units at the periphery of the dendrimers were synthesized for use as artificial inhibitors against Shiga toxins (Stxs) produced by Escherichia coli O157:H7. The galabiose unit, prepared from penta-O-acetyl-beta-D-galactopyranose, was linked with carbosilane dendrimers of three shapes to afford acety I-protected glycodendrimers in good yields. De-O-acetylation of the clusters was carried out in the presence of NaOMe and then aq NaOH to give the desired three shapes of galabiose-coated carbosilane dendrimers. Their biological activities toward Stxs were evaluated by kinetic analysis, binding assays, and cytotoxic assays. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.042