(1S,2S)-4-[1,3]Dioxolan-2-yl-2-methoxymethoxy-1-((3aR,5R,6S,6aR)-6-methoxymethoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-butan-1-ol | 137537-72-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S)-4-[1,3]Dioxolan-2-yl-2-methoxymethoxy-1-((3aR,5R,6S,6aR)-6-methoxymethoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-butan-1-ol
• CAS: 137537-72-5
• 化学式: C₁₈H₃₂O₁₀
• 分子量: 408.446
• InChiKey: GSXDRRJIDNDDMG-CEMYWYHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.36
• 重原子数：
  28.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  103.3
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (1S,2S)-4-[1,3]Dioxolan-2-yl-2-methoxymethoxy-1-((3aR,5R,6S,6aR)-6-methoxymethoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-butan-1-ol 在 sodium azide 、 IR 120 H⁺ resin 、 水 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (3R,4R,5R)-5-[(R)-Azido-((S)-5-hydroxy-tetrahydro-furan-2-yl)-methyl]-tetrahydro-furan-2,3,4-triol
  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：

  2-(2-溴乙基)-1,3-二恶烷 在 四丁基氟化铵 sodium tetrahydroborate 、 重铬酸吡啶 、 水 、 magnesium 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (1S,2S)-4-[1,3]Dioxolan-2-yl-2-methoxymethoxy-1-((3aR,5R,6S,6aR)-6-methoxymethoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-butan-1-ol
  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