| 1389321-10-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1389321-10-1
• 化学式: C₄₀H₄₅NO₉
• 分子量: 683.799
• InChiKey: ALGZZXRCFJMAMV-QRBPUMSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.36
• 重原子数：
  50.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  110.78
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  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：

  2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl chloride 、 3-(苄氧羰基氨基)-1-丙醇 在 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到
  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