(5S,6S)-6-(hydroxymethyl)-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-one | 1373934-58-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5S,6S)-6-(hydroxymethyl)-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-one
• CAS: 1373934-58-7
• 化学式: C₉H₁₅NO₅
• 分子量: 217.222
• InChiKey: OBOFTGTVVADCFL-HZGVNTEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5S,6S)-6-(hydroxymethyl)-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-one 在 2-碘酰基苯甲酸 作用下， 以 乙腈 为溶剂， 以94%的产率得到(5S,6S)-8,8-dimethyl-2-oxo-3,7,9-trioxa-1-azaspiro[4.5]decane-6-carbaldehyde
  参考文献：
  名称：

  A stereoselective total synthesis of the HCl salts of mycestericins F, G and ent-F

  摘要：

  The total synthesis of the HCl salts of two natural sphingolipid-related amino acid derivatives, mycestericins F 4 and G 5 together with unnatural ent-4 center dot HCl, starting from the four crucial scaffolds 6, 8, 9, 11 and utilizing the Wittig reaction to build the C-20 backbone, has been achieved. The selection of selective functional group interconversions accompanied with suitable protection-deprotection protocols in the coupling products 20 and 34 gave the desired structures. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.12.003
• 作为产物：
  描述：

  (4R,5R)-4-[(tert-butyldimethylsilyloxy)methyl]-2,2-dimethyl-1,3-dioxan-5-ol 在 四丁基氟化铵 、 sodium hydride 、 二异丁基氢化铝 、 potassium carbonate 、 臭氧 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 邻二甲苯 、 甲苯 、 乙腈 、 mineral oil 为溶剂， 反应 21.51h， 生成 (5S,6S)-6-(hydroxymethyl)-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-one
  参考文献：
  名称：

  An efficient synthesis of the polar part of sulfamisterin and its analogs

  摘要：

  An efficient synthesis of the polar part of sulfamisterin and its analogs starting from D-xylose is described. The corresponding allylic thiocyanates and trichloroacetimidates were subjected to aza-Claisen rearrangement that effectively generated a quaternary carbon having an amino group as one of the sub-stituents. Subsequent functional group interconversions afforded the highly functionalized branched aminopolyol 29 that is expected to have the crucial application in the construction of sulfamisterin. On the other hand, the second diastereoisomer 34 would be transformed to 2-epi-congener. With respect to the appropriate stereochemical arrangement, the prepared polar segments 29 and 34 can also be utilized for the synthesis of mycestericins (E, G) and their analogs. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.02.019