phenyl 2,6-anhydro-3-O-(diethylisopropylsilyl)-4-O-isobutyryl-3-C-methyl-1,2-dithio-L-mannopyranoside | 151929-61-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: phenyl 2,6-anhydro-3-O-(diethylisopropylsilyl)-4-O-isobutyryl-3-C-methyl-1,2-dithio-L-mannopyranoside
• 英文别名: [(1R,4R,7S,8R)-8-[diethyl(propan-2-yl)silyl]oxy-8-methyl-3-phenylsulfanyl-2-oxa-5-thiabicyclo[2.2.2]octan-7-yl] 2-methylpropanoate
• CAS: 151929-61-2
• 化学式: C₂₄H₃₈O₄S₂Si
• 分子量: 482.781
• InChiKey: HMFCGXFHKRZNPP-MFEKCPQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.36
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  95.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 2,6-anhydro-3-O-(diethylisopropylsilyl)-4-O-isobutyryl-3-C-methyl-1,2-dithio-L-mannopyranoside 在 镍 N-溴代丁二酰亚胺(NBS) 、 MS 4 Angstroem 、 氢气 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 反应 24.67h， 生成 cyclohexyl 2,6-dideoxy-3-O-<2,6-dideoxy-3-O-(2,6-dideoxy-3-O-(diethylisopropylsilyl)-4-O-isobutyryl-3-C-methyl-α-L-arabino-hexopyranosyl)-β-D-arabino-hexopyranosyl>-β-D-arabino-hexopyrnoside
  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
• 作为产物：
  描述：

  苯基硫三甲基硅烷 在 2,6-二甲基吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 phenyl 2,6-anhydro-3-O-(diethylisopropylsilyl)-4-O-isobutyryl-3-C-methyl-1,2-dithio-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

文献信息

• Application of Highly Stereocontrolled Glycosidations Employing 2,6-Anhydro-2-thio Sugars to the Syntheses of Erythromycin A and Olivomycin A Trisaccharide
  作者：Kazunobu Toshima、Yuko Nozaki、Satsuki Mukaiyama、Tetsuro Tamai、Masaya Nakata、Kuniaki Tatsuta、Mitsuhiro Kinoshita

  DOI：10.1021/ja00118a008

  日期：1995.4

  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.
• Total synthesis of the trisaccharide of olivomycin A
  作者：Kazunobu Toshima、Yuko Nozaki、Masaya Nakata、Kuniaki Tatsuta、Mitsuhiro Kinoshita

  DOI：10.1016/s0040-4039(00)73854-8

  日期：1993.9

  The total synthesis of the trisaccharide of olivomycin A, which is one of the aureolic acid antitumor antibiotics, has been achieved. Our approach involves highly stereocontrolled glycosidations using 2,6-ahnydro-2-thio glycosyl donors. The 2,6-anhydro-2-thio trisaccharide 21 was constructed from 4 and 5, and then converted into the 2,6-dideoxy trisaccharide of olivomycin A 3 by hydrogenolysis and

  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。