phenyl 4,6-di-O-benzyl-2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside | 316188-14-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 4,6-di-O-benzyl-2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside
• CAS: 316188-14-4
• 化学式: C₂₉H₃₂O₅S
• 分子量: 492.636
• InChiKey: AYNRGUCTVGHLJX-URYJJRPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.83
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  phenyl 4,6-di-O-benzyl-2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside 在 甲醇 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到phenyl 4,6-di-O-benzyl-1-thio-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
• 作为产物：
  描述：

  苯基1-硫代吡喃己糖苷 在 甲醇 、 camphor-10-sulfonic acid 、 4-甲基苯磺酸吡啶 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 phenyl 4,6-di-O-benzyl-2,3-di-O-isopropylidene-1-thio-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

文献信息

• ——
  作者：Gregor Lemanski、Thomas Ziegler

  DOI：10.1002/1522-2675(20001004)83:10<2655::aid-hlca2655>3.0.co;2-u

  日期：2000.10.4

  A series of prearranged glycosides 5, 17, 23, 28, 37 and 41, having a benzyl-protected 1-thiomannosyl donor linked through its positions 2, 3, 4 and 6 via succinate and malonate tethers, respectively, to positions 2, 3, and 6 of a benzyl glucopyranoside acceptor, were prepared by condensation of the respective mannosyl succinates and malonates with suitably protected benzyl glucopyranosides. The prearranged glycosides were intramolecularly coupled under various conditions to give the corresponding, tethered (1 --> 4)-linked disaccharides The yields and anomer ratios of the products of these couplings were interpreted in terms of the thermodynamic stability of the resulting disaccharides. In the case of prearranged glycoside 17, having positions 3 of both the donor and the acceptor linked by a succinate tether, a strong dependence of the diastereoselectivity of the intramolecular glycosylation on the activation procedure was observed. All other cases did not show a significant dependence of the outcome of the anomeric configuration in intramolecular glycosylation on the activation procedure or the solvent.