(3S,3aR,4R,5S,6R,7aR)-3-azido-4,5-bis(benzyloxy)-6-benzyloxymethyl-2-oxohexahydrofuro[2,3-b]pyran | 1203550-53-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S,3aR,4R,5S,6R,7aR)-3-azido-4,5-bis(benzyloxy)-6-benzyloxymethyl-2-oxohexahydrofuro[2,3-b]pyran
• 英文别名: (3S,3aS,4R,5S,6R,7aR)-3-azido-4,5-dibenzyloxy-6-benzyloxymethyl-2-oxo-hexahydrofuro[2,3-b]pyran；(3S,3aR,4R,5S,6R,7aR)-3-azido-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-3,3a,4,5,6,7a-hexahydrofuro[2,3-b]pyran-2-one
• CAS: 1203550-53-1
• 化学式: C₂₉H₂₉N₃O₆
• 分子量: 515.566
• InChiKey: OQYYDCDCAZVDGY-UTUBKURFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  77.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3S,3aR,4R,5S,6R,7aR)-3-azido-4,5-bis(benzyloxy)-6-benzyloxymethyl-2-oxohexahydrofuro[2,3-b]pyran 在 calcium sulfate 、 水 、 三苯基膦 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 methyl (7S)-3,4,6-tri-O-benzyl-2-deoxy-2-C-[(amino)-(methoxycarbonyl)-methyl]-β-D-glucopyranoside
  参考文献：
  名称：

  Stereoselective diversity-oriented syntheses of functionalized saccharides from bicyclic carbohydrate 1,2-lactones

  摘要：

  Bicyclic carbohydrate 1,2-lactones have been synthesized in only two steps and high yields by saponification and subsequent cyclization from known malonate addition products to glycals. The gluco-configured lactone serves as an important precursor for diversity-oriented syntheses. Thus, stereoselective opening of the lactone ring was realized with various nucleophiles in the presence of Sc(OTf)(3). This enabled the introduction of different substituents at the anomeric position, to afford a broad variety of 1-functionalized carbohydrates. On the other hand, stereoselective alpha-substitution of the gluco-configured lactone with different electrophiles and subsequent ring opening gives a collection of 2-functionalized saccharides. More than 30 products have been isolated in analytically pure form, and their configurations were unequivocally established by various NMR methods. Thus, carbohydrate 1,2-lactones are attractive precursors for the stereoselective synthesis of diverse saccharides. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.069
• 作为产物：
  描述：

  (3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-benzyloxymethyl-2-oxohexahydrofuro[2,3-b]pyran 在 双(三甲基硅烷基)氨基钾 、 2,4,6-三异丙基苯磺酰叠氮化物 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以88%的产率得到(3S,3aR,4R,5S,6R,7aR)-3-azido-4,5-bis(benzyloxy)-6-benzyloxymethyl-2-oxohexahydrofuro[2,3-b]pyran
  参考文献：
  名称：

  Stereodivergent syntheses at the glucose backbone

  摘要：

  两种具有不同官能团的2-C支化碳水化合物的立体异构体可以从相同的丙二酸酯前体中以良好的产率选择性地得到，仅需要几个步骤。

  DOI：

  10.1039/b918893m

文献信息

• Stereodivergent syntheses at the glucose backbone
  作者：Jian Yin、Torsten Linker

  DOI：10.1039/b918893m

  日期：——

  Both diastereomers of 2-C-branched carbohydrates with various functional groups are selectively available from the same malonate precursor in good yields in only a few steps.

  两种具有不同官能团的2-C支化碳水化合物的立体异构体可以从相同的丙二酸酯前体中以良好的产率选择性地得到，仅需要几个步骤。
• Stereoselective diversity-oriented syntheses of functionalized saccharides from bicyclic carbohydrate 1,2-lactones
  作者：Jian Yin、Torsten Linker

  DOI：10.1016/j.tet.2011.01.069

  日期：2011.4

  Bicyclic carbohydrate 1,2-lactones have been synthesized in only two steps and high yields by saponification and subsequent cyclization from known malonate addition products to glycals. The gluco-configured lactone serves as an important precursor for diversity-oriented syntheses. Thus, stereoselective opening of the lactone ring was realized with various nucleophiles in the presence of Sc(OTf)(3). This enabled the introduction of different substituents at the anomeric position, to afford a broad variety of 1-functionalized carbohydrates. On the other hand, stereoselective alpha-substitution of the gluco-configured lactone with different electrophiles and subsequent ring opening gives a collection of 2-functionalized saccharides. More than 30 products have been isolated in analytically pure form, and their configurations were unequivocally established by various NMR methods. Thus, carbohydrate 1,2-lactones are attractive precursors for the stereoselective synthesis of diverse saccharides. (C) 2011 Elsevier Ltd. All rights reserved.