[(2R,3S,4S,5R,6R)-2-[(2S,3S,4S,5R,6R)-4,5-bis(phenylmethoxy)-2-[3-(phenylmethoxycarbonylamino)propoxy]-6-(phenylmethoxymethyl)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate | 1389321-12-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,4S,5R,6R)-2-[(2S,3S,4S,5R,6R)-4,5-bis(phenylmethoxy)-2-[3-(phenylmethoxycarbonylamino)propoxy]-6-(phenylmethoxymethyl)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 1389321-12-3
• 化学式: C₆₇H₇₃NO₁₄
• 分子量: 1116.31
• InChiKey: VNVWMMQVTXVKEQ-KIILYTISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  82
• 可旋转键数：
  32
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  157
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4S,5R,6R)-2-[(2S,3S,4S,5R,6R)-4,5-bis(phenylmethoxy)-2-[3-(phenylmethoxycarbonylamino)propoxy]-6-(phenylmethoxymethyl)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate 在 甲醇 、 sodium methylate 作用下， 以94%的产率得到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 在 甲醇 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 生成 [(2R,3S,4S,5R,6R)-2-[(2S,3S,4S,5R,6R)-4,5-bis(phenylmethoxy)-2-[3-(phenylmethoxycarbonylamino)propoxy]-6-(phenylmethoxymethyl)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate
  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