methyl 2,6-anhydro-3-C-methyl-2-thio-β-L-mannopyranoside | 151929-68-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,6-anhydro-3-C-methyl-2-thio-β-L-mannopyranoside
• CAS: 151929-68-9
• 化学式: C₈H₁₄O₄S
• 分子量: 206.263
• InChiKey: ZUSZLBCXLIYTLJ-DMHSOCPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.41
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 2,6-anhydro-3-C-methyl-2-thio-β-L-mannopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 β-phenyl 2,6-anhydro-4-O-isobutyryl-3-C-methyl-1,2-dithio-L-mannopyranoside
  参考文献：
  名称：

  Application of Highly Stereocontrolled Glycosidations Employing 2,6-Anhydro-2-thio Sugars to the Syntheses of Erythromycin A and Olivomycin A Trisaccharide

  摘要：

  The highly efficient syntheses of the erythromycin A (1) from its aglycon, (9S)-9-dihydroerythronolide A (4), and the C-D-E trisaccharide 3 of olivomycin A have been accomplished by the successful application of stereocontrolled glycosidations using 2,6-anhydro-2-thio sugars. The former synthesis includes the highly alpha-stereoselective glycosidation of the C5 desosaminated lactone 12 with phenyl 2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-1 ,2-dithio-L-altropyranoside (10), which was achieved by using NIS-TfOH. The latter synthesis involves both the highly beta-stereoselective glycosidation of 1,3-di-O-acetyl-2,6-anhydro-4-O-benzyl-2-thio-beta-D-altropy (23), which was realized by employing TMSOTf, and the highly alpha-stereoselective glycosidation of phenyl 2,6-anhydro-3-O-(diethylisopropylsilyl) -4-O-isobutyryl-3-C-methyl-1,2-dithio-L-manno-pyranoside (24), which succeeded by utilizing NBS. Hydrogenolyses using Raney Ni as a catalyst and selective deprotections of the key glyco substances 17 and 22 led to the total syntheses of erythromycin A (1) and the C-D-E trisaccharide 3 of olivomycin A, respectively.

  DOI：

  10.1021/ja00118a008
• 作为产物：
  描述：

  methyl 2,6-anhydro-4-O-benzyl-3-C-methyl-2-thio-β-L-mannopyranoside 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以75%的产率得到methyl 2,6-anhydro-3-C-methyl-2-thio-β-L-mannopyranoside
  参考文献：
  名称：

  寡霉素A三糖的全合成

  摘要：

  已经实现了作为金黄色酸抗肿瘤抗生素之一的寡霉素A的三糖的全合成。我们的方法涉及使用2，6-邻氨基-2-硫代糖基供体的高度立体控制的糖苷化。由4和5构造2，6-脱水-2-硫代三糖21，然后通过氢解和脱保护将其转化成寡霉素A 3的2，6-二脱氧三糖。

  DOI：

  10.1016/s0040-4039(00)73854-8