diazoacetic acid 1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranos-5-yl ester | 946853-69-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diazoacetic acid 1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranos-5-yl ester
• 英文别名: [(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl 2-diazoacetate
• CAS: 946853-69-6
• 化学式: C₁₁H₁₆N₂O₆
• 分子量: 272.258
• InChiKey: KONVQANAVMKLBS-PEBGCTIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  65.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  苯乙烯 、 diazoacetic acid 1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranos-5-yl ester 在 chiral bis(oxazoline) 、 三氟甲烷磺酸亚铜(I)苯联合体 (2:1) 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 17.0h， 生成 [(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl (1R,2R)-2-phenylcyclopropane-1-carboxylate 、 [(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl (1S,2S)-2-phenylcyclopropane-1-carboxylate 、 、
  参考文献：
  名称：

  Asymmetric cyclopropanation with diazoacetates induced by carbohydrate-derived chiral auxiliaries

  摘要：

  alpha-Diazoacetates with carbohydrate-based chiral auxiliaries have been synthesized and screened in the asymmetric cyclopropanation of styrene in connection with the effect of the chiral Cu(I)-catalyzed reaction, showing the remarkable importance of the carbohydrate-based chiral auxiliaries on the enantioselectivities and an unexpected effect on the trans:cis ratios. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.04.027
• 作为产物：
  描述：

  [(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl 3-oxobutanoate 在 lithium hydroxide 、 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 72.0h， 生成 diazoacetic acid 1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranos-5-yl ester
  参考文献：
  名称：

  Asymmetric cyclopropanation with diazoacetates induced by carbohydrate-derived chiral auxiliaries

  摘要：

  alpha-Diazoacetates with carbohydrate-based chiral auxiliaries have been synthesized and screened in the asymmetric cyclopropanation of styrene in connection with the effect of the chiral Cu(I)-catalyzed reaction, showing the remarkable importance of the carbohydrate-based chiral auxiliaries on the enantioselectivities and an unexpected effect on the trans:cis ratios. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.04.027