1(R),5(S),4'(R),8(S)-8-<4'-(methyl 2,3-O-isopropylidene-β-D-erythro-furanosidyl)>-1-aza-7-oxa-4-thiadioxybicyclo<3.2.1>octane

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1(R),5(S),4'(R),8(S)-8-<4'-(methyl 2,3-O-isopropylidene-β-D-erythro-furanosidyl)>-1-aza-7-oxa-4-thiadioxybicyclo<3.2.1>octane
• 英文别名: 1(R),5(S),4'(R),8(S)-8-[4'-(methyl 2,3-O-isopropylidene-β-D-erythro-furanosidyl)]-1-aza-7-oxa-4-thiadioxybicyclo[3.2.1]octane；(5S,8S)-8-[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-7-oxa-4lambda6-thia-1-azabicyclo[3.2.1]octane 4,4-dioxide；(5S,8S)-8-[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-7-oxa-4λ6-thia-1-azabicyclo[3.2.1]octane 4,4-dioxide
• 化学式: C₁₃H₂₁NO₇S
• 分子量: 335.378
• InChiKey: PJVZXRVTZDSIHK-PAUJSFGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  91.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde 在 盐酸羟胺 作用下， 以 吡啶 、 甲醇 、 水 、 甲苯 为溶剂， 反应 72.0h， 生成 1(R),5(S),4'(R),8(S)-8-<4'-(methyl 2,3-O-isopropylidene-β-D-erythro-furanosidyl)>-1-aza-7-oxa-4-thiadioxybicyclo<3.2.1>octane
  参考文献：
  名称：

  Homochiral cycloadducts derived from sugar aldoximes via nitrone intermediates

  摘要：

  Tandem nitrone generation/cycloaddition reactions between simple sugar aldoximes and divinyl sulphone in refluxing toluene have been shown to occur regiospecifically and with high diastereoselectivity in the cycloaddition step to afford homochiral cycloadducts in good yield. The process is applicable to both furanose and pyranose aldoximes. Absolute stereochemistries of the products have been determined by NOE spectroscopy and X-ray crystallography.

  DOI：

  10.1016/s0040-4020(01)80704-3