methyl β-L-ossaminide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl β-L-ossaminide
• 英文别名: (2S,3S,6S)-6-methoxy-N,N,2-trimethyloxan-3-amine
• 化学式: C₉H₁₉NO₂
• 分子量: 173.255
• InChiKey: BKKBOCHIPICUMP-CIUDSAMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 methyl 4-amino-2,3,4,6-tetradeoxy-L-threo-hexopyranoside 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 methyl α-L-ossaminide 、 methyl β-L-ossaminide
  参考文献：
  名称：

  Spinosyn G:  Proof of Structure by Semisynthesis

  摘要：

  Spinosyn G was isolated in the late 1980s as a minor component from the broth of our potent, fermentation-derived insecticide spinosad. Its structure was then tentatively identified as 5"-epispinosyn A (3) on the basis of H-1 and C-13 NMR data, but the 4"-epi compound 4 could not be conclusively ruled out with the data available. Described herein are unambiguous syntheses of both 3 and 4, whereby 3 was proved identical to the natural product. Compound 4 was prepared from intact spinosyn A by a novel F-TEDA-promoted oxidative deamination to the 4"-ketone 5, stereoselective reduction to the equatorial alcohol 6, and nitrogen incorporation via the axial azide 7. Compound 3 was obtained by coupling spinosyn A 17-pseudoaglycone (9) with the N-protected dihydropyran 16 derived from methyl L-ossaminide (14). This gave an similar to 2:1 mixture of anomeric products 17 with the desired equatorial glycoside predominating, which was then converted to 3 by N-deprotection and methylation.

  DOI：

  10.1021/jo048173k