(9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide | 138505-43-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide
• 英文别名: (9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-5-O-[2-O-(methoxycarbonyl)-β-D-desosaminyl]erythronolide A N-Oxide
• CAS: 138505-43-8
• 化学式: C₄₆H₇₅NO₁₆S
• 分子量: 930.165
• InChiKey: JBIHWXAEFVVRAW-LWVBIYBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.31
• 重原子数：
  64.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  221.19
• 氢给体数：
  4.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  (9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide 在 Raney-Ni (W₄) 氢气 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 0.17h， 生成 (9S)-9-dihydroerythromycin A N-oxide
  参考文献：
  名称：

  有效的2,6-脱水-2-硫代糖基糖基化在红霉素A全合成中的应用

  摘要：

  由（9S）-9-二氢赤藓醇内酯A（2）合成红霉素A（I），是通过2,6-脱水-2-硫代糖9的高度立体选择性和强力糖基化作为关键步骤而有效地实现的。

  DOI：

  10.1016/0040-4039(91)80777-4
• 作为产物：
  描述：

  phenyl 2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-1,2-dithio-β-L-altro-pyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 12.17h， 生成 (9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide
  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