[(1S,2S)-1-[(3aR,5S,6S,6aR)-6-(methoxymethoxy)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-4-(1,3-dioxolan-2-yl)-2-(methoxymethoxy)butoxy]-tert-butyl-dimethylsilane | 137537-71-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(1S,2S)-1-[(3aR,5S,6S,6aR)-6-(methoxymethoxy)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-4-(1,3-dioxolan-2-yl)-2-(methoxymethoxy)butoxy]-tert-butyl-dimethylsilane
• CAS: 137537-71-4
• 化学式: C₂₄H₄₆O₁₀Si
• 分子量: 522.709
• InChiKey: TVXLTUUBIHBWOL-MYXQZSHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  35.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  92.3
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  [(1S,2S)-1-[(3aR,5S,6S,6aR)-6-(methoxymethoxy)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-4-(1,3-dioxolan-2-yl)-2-(methoxymethoxy)butoxy]-tert-butyl-dimethylsilane 在 四丁基氟化铵 sodium azide 、 水 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3aR,5R,6S,6aR)-5-[(1R,2S)-1-azido-4-(1,3-dioxolan-2-yl)-2-(methoxymethoxy)butyl]-6-(methoxymethoxy)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
  参考文献：
  名称：

  First synthesis of (1R,2R,3S,9S,9aR)-1,2,3,9-tetrahydroxy-quinolizidine, a novel isosteric homologue of the glucosidase inhibitor castanospermine

  摘要：

  The reaction of 5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-beta-L-ido-hexodialdodifuranose, prepared from D-glucofuranurono-6,3-lactone in four highly efficient steps, with the Grignard reagent generated from 2-(2-bromoethyl)-1,3-dioxolane gave a protected nonodialdose which was transformed into a tetrahydroxyquinolizidine essentially isosteric and homologous with castanospermine.

  DOI：

  10.1016/s0040-4039(00)93488-9
• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 重铬酸吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 [(1S,2S)-1-[(3aR,5S,6S,6aR)-6-(methoxymethoxy)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-4-(1,3-dioxolan-2-yl)-2-(methoxymethoxy)butoxy]-tert-butyl-dimethylsilane
  参考文献：
  名称：

  First synthesis of (1R,2R,3S,9S,9aR)-1,2,3,9-tetrahydroxy-quinolizidine, a novel isosteric homologue of the glucosidase inhibitor castanospermine

  摘要：

  The reaction of 5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-beta-L-ido-hexodialdodifuranose, prepared from D-glucofuranurono-6,3-lactone in four highly efficient steps, with the Grignard reagent generated from 2-(2-bromoethyl)-1,3-dioxolane gave a protected nonodialdose which was transformed into a tetrahydroxyquinolizidine essentially isosteric and homologous with castanospermine.

  DOI：

  10.1016/s0040-4039(00)93488-9