benzyl (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6R)-6-(2-azidoethyl)-5-methoxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-3-hydroxy-4,5-dimethoxyoxane-2-carboxylate | 511511-40-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6R)-6-(2-azidoethyl)-5-methoxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-3-hydroxy-4,5-dimethoxyoxane-2-carboxylate
• CAS: 511511-40-3
• 化学式: C₃₈H₄₇N₃O₁₁
• 分子量: 721.805
• InChiKey: KFJQFUQONOZQIR-IGGORAQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  52
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  benzyl (2S,3S,4S,5R,6R)-6-[(2R,3R,4S,5R)-4-acetyloxy-2-(acetyloxymethyl)-5-phenylmethoxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl]oxy-3-[(2R,3R,4S,5R,6R)-6-(acetyloxymethyl)-3,4,5-trimethoxyoxan-2-yl]oxy-4,5-dimethoxyoxane-2-carboxylate 、 benzyl (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6R)-6-(2-azidoethyl)-5-methoxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-3-hydroxy-4,5-dimethoxyoxane-2-carboxylate 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以77%的产率得到benzyl (2S,3S,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-4-acetyloxy-2-(acetyloxymethyl)-6-[(2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6R)-6-(2-azidoethyl)-5-methoxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-4,5-dimethoxy-2-phenylmethoxycarbonyloxan-3-yl]oxy-5-phenylmethoxyoxan-3-yl]oxy-3-[(2R,3R,4S,5R,6R)-6-(acetyloxymethyl)-3,4,5-trimethoxyoxan-2-yl]oxy-4,5-dimethoxyoxane-2-carboxylate
  参考文献：
  名称：

  Probing the Heparin−Antithrombin III Interaction Using Synthetic Pentasaccharides Bearing Positively Charged Groups

  摘要：

  Four heparin pentasaccharides bearing either one (i.e. 3b and 4b) or two (i.e. 3c and 4c) positively charged amino groups at the reducing end have been synthesized and evaluated for their antithrombin III mediated anti-Xa activity. The positively charged groups were introduced to interact specifically with the negatively charged amino acid residues Glu113 and Asp 117 of antithrombin III, which are located in the heparin binding. site in close proximity to the reducing end of the saccharide. It turned out that the target compounds 3b,c and 4b,c exhibited relatively low anti-Xa activities, indicating unfavorable interactions between the new pentasaccharides and antithrombin III rather than the anticipated enhancement of association. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

  DOI：

  10.1002/1099-0690(200212)2002:23<3954::aid-ejoc3954>3.0.co;2-2
• 作为产物：
  描述：

  ((1S,3R,4R,5R,6R)-5-Benzyloxy-3-benzyloxymethyl-2,7-dioxa-bicyclo[4.1.0]hept-4-yloxy)-tert-butyl-dimethyl-silane 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 吡啶 、 N-碘代丁二酰亚胺 、 lithium aluminium tetrahydride 、 sodium azide 、 2-甲基-2-丁烯 、 三氟甲磺酸 、 4 A molecular sieve 、 硼烷 、 potassium tert-butylate 、 四丁基氟化铵 、 四丁基氯化铵 、 sodium hydride 、 碳酸氢钠 、 potassium hydrogencarbonate 、 对甲苯磺酸 、 溶剂黄146 、 potassium bromide 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 34.58h， 生成 benzyl (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6R)-6-(2-azidoethyl)-5-methoxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-3-hydroxy-4,5-dimethoxyoxane-2-carboxylate
  参考文献：
  名称：

  Probing the Heparin−Antithrombin III Interaction Using Synthetic Pentasaccharides Bearing Positively Charged Groups

  摘要：

  Four heparin pentasaccharides bearing either one (i.e. 3b and 4b) or two (i.e. 3c and 4c) positively charged amino groups at the reducing end have been synthesized and evaluated for their antithrombin III mediated anti-Xa activity. The positively charged groups were introduced to interact specifically with the negatively charged amino acid residues Glu113 and Asp 117 of antithrombin III, which are located in the heparin binding. site in close proximity to the reducing end of the saccharide. It turned out that the target compounds 3b,c and 4b,c exhibited relatively low anti-Xa activities, indicating unfavorable interactions between the new pentasaccharides and antithrombin III rather than the anticipated enhancement of association. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

  DOI：

  10.1002/1099-0690(200212)2002:23<3954::aid-ejoc3954>3.0.co;2-2

文献信息

• Probing the Heparin−Antithrombin III Interaction Using Synthetic Pentasaccharides Bearing Positively Charged Groups
  作者：Jeroen D. C. Codée、Gijsbert A. van der Marel、Constant A. A. van Boeckel、Jacques H. van Boom

  DOI：10.1002/1099-0690(200212)2002:23<3954::aid-ejoc3954>3.0.co;2-2

  日期：2002.12

  Four heparin pentasaccharides bearing either one (i.e. 3b and 4b) or two (i.e. 3c and 4c) positively charged amino groups at the reducing end have been synthesized and evaluated for their antithrombin III mediated anti-Xa activity. The positively charged groups were introduced to interact specifically with the negatively charged amino acid residues Glu113 and Asp 117 of antithrombin III, which are located in the heparin binding. site in close proximity to the reducing end of the saccharide. It turned out that the target compounds 3b,c and 4b,c exhibited relatively low anti-Xa activities, indicating unfavorable interactions between the new pentasaccharides and antithrombin III rather than the anticipated enhancement of association. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).