3-[(N-benzyloxycarbonyl)amino]propyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside | 1389321-11-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[(N-benzyloxycarbonyl)amino]propyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside
• 英文别名: benzyl N-[3-[(2S,3S,4R,5R,6R)-3-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxypropyl]carbamate
• CAS: 1389321-11-2
• 化学式: C₃₈H₄₃NO₈
• 分子量: 641.761
• InChiKey: VLXUZQKJWFIZKI-ORIAJCIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  47
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-[(N-benzyloxycarbonyl)amino]propyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 甲醇 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 生成 benzyl N-[3-[(2S,3S,4S,5R,6R)-3-[(2R,3S,4R,5R,6R)-3-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxypropyl]carbamate
  参考文献：
  名称：

  Facile construction of 1,2-cis glucosidic linkage using sequential oxidation–reduction route for synthesis of an ER processing α-glucosidase I substrate

  摘要：

  The fluorescence-labeled hexasaccharide (Glc alpha 1-2Glc alpha 1-3Glc alpha 1-3Man alpha 1-2Man alpha 1-2Man alpha) was synthesized as a substrate for the processing enzyme alpha-glucosidase I. To construct the 1,2-cis glucosidic linkages, we employed an alpha stereoselective coupling using the mannosyl donor by assisted neighboring-group participation, followed by conversion of the stereochemistry of the C-2 hydroxyl group in the mannose residue using sequential oxidation of C-2 hydroxyl group to a 2-keto group and stereoselective reduction of the hydroxyl group to the gluco-configuration to provide the corresponding alpha-glucoside derivative. Using this strategy, the three consecutive alpha-glucosidic linkages were easily obtained in a stereoselective manner. Finally, the Dansyl labeled hexasaccharide derivative was used to measure the activity of processing alpha-glucosidase I. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.061
• 作为产物：
  描述：

  3-(苄氧羰基氨基)-1-丙醇 在 甲醇 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 生成 3-[(N-benzyloxycarbonyl)amino]propyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Facile construction of 1,2-cis glucosidic linkage using sequential oxidation–reduction route for synthesis of an ER processing α-glucosidase I substrate

  摘要：

  The fluorescence-labeled hexasaccharide (Glc alpha 1-2Glc alpha 1-3Glc alpha 1-3Man alpha 1-2Man alpha 1-2Man alpha) was synthesized as a substrate for the processing enzyme alpha-glucosidase I. To construct the 1,2-cis glucosidic linkages, we employed an alpha stereoselective coupling using the mannosyl donor by assisted neighboring-group participation, followed by conversion of the stereochemistry of the C-2 hydroxyl group in the mannose residue using sequential oxidation of C-2 hydroxyl group to a 2-keto group and stereoselective reduction of the hydroxyl group to the gluco-configuration to provide the corresponding alpha-glucoside derivative. Using this strategy, the three consecutive alpha-glucosidic linkages were easily obtained in a stereoselective manner. Finally, the Dansyl labeled hexasaccharide derivative was used to measure the activity of processing alpha-glucosidase I. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.061