2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1<*>4)-S-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1<*>1)-(2R,3R,4E)-3-benzyloxy-2-dichloroacetamido-4-octadecen-1-thiol | 173067-94-2

• 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: 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1<*>4)-S-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1<*>1)-(2R,3R,4E)-3-benzyloxy-2-dichloroacetamido-4-octadecen-1-thiol
• CAS: 173067-94-2
• 化学式: C₅₃H₇₅Cl₂NO₂₀S
• 分子量: 1149.15
• InChiKey: CWMSUBDOQHABJI-AGGGJWGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.11
• 重原子数：
  77.0
• 可旋转键数：
  32.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  267.19
• 氢给体数：
  1.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1<*>4)-S-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1<*>1)-(2R,3R,4E)-3-benzyloxy-2-dichloroacetamido-4-octadecen-1-thiol 在 甲醇 、 氢氧化钾 作用下， 反应 3.0h， 以89%的产率得到β-D-galactopyranosyl-(1<*>4)-S-β-D-glucopyranosyl-(1<*>1)-(2R,3R,4E)-2-amino-3-hydroxy-4-octadecen-1-thiol
  参考文献：
  名称：

  Synthesis of fluorescent and radioactive analogues of two lactosylceramides and glucosylceramide containing β-thioglycosidic bonds that are resistant to enzymatic degradation

  摘要：

  Condensation of 2-S-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-2-thiopseudourea hydrobromide with 2,3,6-tri-O-benzoyl-4-O-trifluoromethylsulfonyl-beta-D-galactopyranosy-(1-->1)-(2S,3R,4E)-3-O-benzoyl-2-dichloroacetamido-4-octadecan afforded S-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-(1-->4)-2,3,6-tri-O-benzoyl-4-thio-beta-D-glucopyranosyl-(1-->1)-(2S, 3R,4E)-3-O-benzoyl-2-dichloroacetamido-4 in good yield. Removal of the protecting groups, followed by selective N-acylation of the sphingosine amino group with either a fluorescent or a radioactive fatty acid, gave labeled lactosylceramide analogues in good yield. Since these products contained a beta-thioglycosidic bond between the two sugar moieties, they were totally resistant to the action of acid lysosomal glycosidases. Likewise, condensation of 2-S(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosy hydrobromide and 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl-(1-->4)-2,3,6-tri-O- acetyl-1-S-acetyl-1-thio-beta-D-glucopyranose with (2R,3R,4E)-3-O-benzoyl-2-dichloroacetamido-1-iodo-4-octadecen-3-ol in methanolic sodium acetate afforded the corresponding beta-thioglycosides 14 and 16, respectively, in good yield. These beta-thioglycosides were converted into glucosylceramide and lactosylceramide analogues following removal of the protecting groups and by subsequent selective N-acylation using either a fluorescent or radioactive fatty acid N-succinimidyl ester. Whereas the glucosylthioceramides thus obtained proved to be completely undegradable by lysosomal glucocerebrosidase, the lactosylceramides containing the beta-thioglycosidic bond between the lactose and the ceramide residues could be degraded by lysosomal GM1-beta-galactosidase to give the corresponding glucosylthioceramides. These compounds did not yield to any further enzymatic degradation.

  DOI：

  10.1016/0008-6215(95)00189-z
• 作为产物：
  描述：

  (2S,3R,4E)-3-O-benzoyl-1-O-tert-butyldiphenylsilyl-2-dichloroacetamido-4-octadecen-1,3-diol 在 吡啶 、 四丁基氟化铵 、 sodium acetate 、 sodium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 27.0h， 生成 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1<*>4)-S-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1<*>1)-(2R,3R,4E)-3-benzyloxy-2-dichloroacetamido-4-octadecen-1-thiol
  参考文献：
  名称：

  Synthesis of fluorescent and radioactive analogues of two lactosylceramides and glucosylceramide containing β-thioglycosidic bonds that are resistant to enzymatic degradation

  摘要：

  Condensation of 2-S-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-2-thiopseudourea hydrobromide with 2,3,6-tri-O-benzoyl-4-O-trifluoromethylsulfonyl-beta-D-galactopyranosy-(1-->1)-(2S,3R,4E)-3-O-benzoyl-2-dichloroacetamido-4-octadecan afforded S-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-(1-->4)-2,3,6-tri-O-benzoyl-4-thio-beta-D-glucopyranosyl-(1-->1)-(2S, 3R,4E)-3-O-benzoyl-2-dichloroacetamido-4 in good yield. Removal of the protecting groups, followed by selective N-acylation of the sphingosine amino group with either a fluorescent or a radioactive fatty acid, gave labeled lactosylceramide analogues in good yield. Since these products contained a beta-thioglycosidic bond between the two sugar moieties, they were totally resistant to the action of acid lysosomal glycosidases. Likewise, condensation of 2-S(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosy hydrobromide and 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl-(1-->4)-2,3,6-tri-O- acetyl-1-S-acetyl-1-thio-beta-D-glucopyranose with (2R,3R,4E)-3-O-benzoyl-2-dichloroacetamido-1-iodo-4-octadecen-3-ol in methanolic sodium acetate afforded the corresponding beta-thioglycosides 14 and 16, respectively, in good yield. These beta-thioglycosides were converted into glucosylceramide and lactosylceramide analogues following removal of the protecting groups and by subsequent selective N-acylation using either a fluorescent or radioactive fatty acid N-succinimidyl ester. Whereas the glucosylthioceramides thus obtained proved to be completely undegradable by lysosomal glucocerebrosidase, the lactosylceramides containing the beta-thioglycosidic bond between the lactose and the ceramide residues could be degraded by lysosomal GM1-beta-galactosidase to give the corresponding glucosylthioceramides. These compounds did not yield to any further enzymatic degradation.

  DOI：

  10.1016/0008-6215(95)00189-z