| 1185735-71-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1185735-71-0
• 化学式: C₁₉H₂₀O₅S
• 分子量: 360.431
• InChiKey: BDNIQCYVYFGHSI-SGYMCOKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 phenyl 2-O-acetyl-4,6-O-benzyliden-1-thio-β-D-gulopyranoside
  参考文献：
  名称：

  Synthesis of 3-azido-3-deoxy-β-d-galactopyranosides

  摘要：

  Three efficient routes to 3-azido-3-deoxy-beta-D-galactopyranosides were developed relying on a double inversion protocol at C3. Two of the routes were demonstrated to work with both O- and S-glycosides. In all three routes, the 2-O-acetyl-3-azido-4,6-O-benzylidene-3-deoxy-beta-D-galactopyranosides were obtained by an azide inversion of the key intermediates 2-O-acetyl-4,6-O-benzylidene-3-O-trifluoromethanesulfonyl-beta-D-gulopyranosides. The intermediate gulopyranosides were in turn obtained from 2-O-acetyl-4,6-O-benzylidene-3-O-trifluoromethanesulfonyl-beta-D-galactopyranosides, installed in one pot from the 4,6-O-benzylidene-beta-D-galactopyranosides, by inversion with nitrite or acetate. For O-glycosides, the gulopyranoside configuration could alternatively be obtained from the 4,6-O-benzylidene-beta-D-galactopyranoside by elimination to give the 2,3-dianhydro derivative followed by a highly stereoselective cis-dihydroxylation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.05.005
• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 以98%的产率得到
  参考文献：
  名称：

  Synthesis of 3-azido-3-deoxy-β-d-galactopyranosides

  摘要：

  Three efficient routes to 3-azido-3-deoxy-beta-D-galactopyranosides were developed relying on a double inversion protocol at C3. Two of the routes were demonstrated to work with both O- and S-glycosides. In all three routes, the 2-O-acetyl-3-azido-4,6-O-benzylidene-3-deoxy-beta-D-galactopyranosides were obtained by an azide inversion of the key intermediates 2-O-acetyl-4,6-O-benzylidene-3-O-trifluoromethanesulfonyl-beta-D-gulopyranosides. The intermediate gulopyranosides were in turn obtained from 2-O-acetyl-4,6-O-benzylidene-3-O-trifluoromethanesulfonyl-beta-D-galactopyranosides, installed in one pot from the 4,6-O-benzylidene-beta-D-galactopyranosides, by inversion with nitrite or acetate. For O-glycosides, the gulopyranoside configuration could alternatively be obtained from the 4,6-O-benzylidene-beta-D-galactopyranoside by elimination to give the 2,3-dianhydro derivative followed by a highly stereoselective cis-dihydroxylation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.05.005