2-(prop-2-ynylcarbamoyl)ethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside | 1326719-91-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(prop-2-ynylcarbamoyl)ethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-[3-oxo-3-(prop-2-ynylamino)propyl]sulfanyloxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 1326719-91-8
• 化学式: C₃₂H₄₃NO₁₈S
• 分子量: 761.755
• InChiKey: RMGKMHYQVZNTFE-HSUAEPONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  52
• 可旋转键数：
  23
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  266
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  2-(prop-2-ynylcarbamoyl)ethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside 、 5,11,17,23-tetrakis-(6-azidohexanamido)-25,26,27,28-tetrakis-[2-(2-(2-methoxyethoxy)ethoxy)ethoxy]-calix[4]arene 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以80%的产率得到5,11,17,23-tetrakis(5-(4-(2-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranosyl)thio]ethylcarbamoyl)-1H-1,2,3-triazol-1-yl)pentylcarbamoyl)-25,26,27,28-tetrakis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-calix[4]arene
  参考文献：
  名称：

  Glycoclusters presenting lactose on calix[4]arene cores display trypanocidal activity

  摘要：

  A new series of water-soluble tetravalent glycoclusters incorporating beta-lactosyl residues attached to a central calix[4]arene core was synthesised using azide-alkyne Cu(I)-catalysed cycloaddition ('click chemistry'). Carbohydrate moieties were attached either to the upper or lower rim of rigid cone-shaped or partial cone macrocycles via 14-21 atom spacer arms. The glycoclusters with a C(4)-symmetrical arrangement of beta-lactosyl residues showed trypanocidal activity, with one of them showing comparable activity to established anti-trypanosomal drug benznidazole in in vitro anti-parasite assays. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.065
• 作为产物：
  描述：

  炔丙胺 、 3-[(2S,3R,4S,5R,6R)-3,4-Diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylsulfanyl]-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester 以 二氯甲烷 为溶剂， 反应 17.0h， 以62%的产率得到2-(prop-2-ynylcarbamoyl)ethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Glycoclusters presenting lactose on calix[4]arene cores display trypanocidal activity

  摘要：

  A new series of water-soluble tetravalent glycoclusters incorporating beta-lactosyl residues attached to a central calix[4]arene core was synthesised using azide-alkyne Cu(I)-catalysed cycloaddition ('click chemistry'). Carbohydrate moieties were attached either to the upper or lower rim of rigid cone-shaped or partial cone macrocycles via 14-21 atom spacer arms. The glycoclusters with a C(4)-symmetrical arrangement of beta-lactosyl residues showed trypanocidal activity, with one of them showing comparable activity to established anti-trypanosomal drug benznidazole in in vitro anti-parasite assays. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.065