rac-(ethyl carbonic) 2-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-methylpropanoic anhydride | 136029-25-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: rac-(ethyl carbonic) 2-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-methylpropanoic anhydride
• CAS: 136029-25-9
• 化学式: C₁₅H₂₄O₈
• 分子量: 332.351
• InChiKey: JILGMUCROIMDIG-YTWAJWBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  rac-(ethyl carbonic) 2-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-methylpropanoic anhydride 在 sodium azide 作用下， 以 水 、 丙酮 、 苯 为溶剂， 反应 6.17h， 生成 methyl 5,6-dideoxy-5-isocyanato-2,3-O-isopropylidene-5-C-methyl-β-L-ribo-hexofuranoside
  参考文献：
  名称：

  Total, asymmetric synthesis of hexoses and azasugars branched at C(5).

  摘要：

  The Diels-Alder adduct (-)-5 (a "naked sugar") of furan to 1-cyanovinyl (1R')-camphanate was converted into (+)-(1R,5S,6S,7S)-6-exo,7-exo-(isopropylidenedioxy)-2,8-dioxabicylo[3.2.1]octan-3-one and into (+)-(1R,5S,6S,7S)-7-endo-(benzyloxy)-6-exo-{[(t-butyl)dimethylsilyl]oxy}-2,8-dioxabicyclo[3.2.1]-octan-3-one ((+)-17). Double methylation at C(4) gave the corresponding 5-deoxy-5-C-dimethyl furanurono-6,1-lactones (+)-42 and (+)-19, respectively. Stereoselective and successive methylation and benzyloxymethylation of (+)-(1R,5S,6S,7S)-6-exo,-7-exo-(isopropylidenedioxy)2,8-dioxabicyclo[3.2.1]octan-3-one gave (+)-(1R,4R,5S,6S,7S)4-exo-[(benzyloxy)methyl]-6-exo,7-exo-(isopropylidenedioxy)-4-endo-methyl-2,8-dioxabicyclo[3.2.1]octan-3-one ((+)-9). Highly stereoselective oxydative decarboxylation of lactones (+)-9 and (+)-19 led to 5-C-methyl-alpha-beta-D-talo-hexose ((-)-1) and to 6-deoxy-5-C-methyl-alpha-beta-L-arabino-hexose ((-)-2), respectively. Transformation of lactones (+)-9 and (+)-42 into the corresponding acyl azides and their Curtius rearrangements led to (5-ammonio-1,5-N-anhydro-5-deoxy-5-C-methyl-alpha-beta-D-talo-hexitol)-1-sulfonate ((+)-3) and to (5-ammonio-1,5-N-anhydro-5,6-dideoxy-5-C-methyl-alpha-beta-L-ribo-hexitol)1-sulfonate ((+)-4), respectively.

  DOI：

  10.1016/s0040-4020(01)91030-0
• 作为产物：
  描述：

  2,8-dioxabicyclo<2.2.1>octane-6,7-diol-3-one, isopropyl acetal 在 Nafion 117 、 氢氧化钾 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 四氯化碳 、 水 、 丙酮 为溶剂， 反应 253.0h， 生成 rac-(ethyl carbonic) 2-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-2-methylpropanoic anhydride
  参考文献：
  名称：

  Asymmetric total synthesis of azasugars branched at C-5

  摘要：

  The new azasugars (5-ammonio-1,5-N-anhydro-5,6-dideoxy-5-C-methyl-alpha-beta-L-ribo-hexitol)-1-sulfonate and (5-ammonio-1,5-N-anhydro-5-deoxy-5-C-methyl-alpha-beta-D-talo-hexitol)-1-sulfonate have been derived from (1S,2R,4S)-2-cyano-7-oxabicyclo[2.2.1]hept-5-en-2-yl (1R')-camphanate.

  DOI：

  10.1016/s0040-4039(00)79713-9