5-acetylthiopentyl (2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-galactopyranoside | 893428-58-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-acetylthiopentyl (2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-4,5-diacetyloxy-6-(5-acetylsulfanylpentoxy)-3-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 893428-58-5
• 化学式: C₃₃H₄₈O₁₉S
• 分子量: 780.799
• InChiKey: GDQXQBSHNYWLHZ-NAFJBVMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  53
• 可旋转键数：
  26
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  263
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  tris(3-((3-bromopropyl)dimethylsilyl)propyl)methylsilane 、 5-acetylthiopentyl (2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-galactopyranoside 、 乙酸酐 在 sodium methylate 、 吡啶 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 以86%的产率得到[(2R,3S,4S,5R,6R)-4,5-diacetyloxy-6-[5-[3-[3-[bis[3-[3-[5-[(2R,3R,4S,5S,6R)-3,4-diacetyloxy-6-(acetyloxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxypentylsulfanyl]propyl-dimethylsilyl]propyl]-methylsilyl]propyl-dimethylsilyl]propylsulfanyl]pentoxy]-3-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
  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 (2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-galactopyranoside 、 硫代乙酸 在 偶氮二异丁腈 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以93%的产率得到5-acetylthiopentyl (2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-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