acetylacetate de di-O-isopropylidene-2,3:4,5 β-D fructopyranose | 123533-14-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: acetylacetate de di-O-isopropylidene-2,3:4,5 β-D fructopyranose
• 英文别名: [(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methyl 3-oxobutanoate
• CAS: 123533-14-2
• 化学式: C₁₆H₂₄O₈
• 分子量: 344.362
• InChiKey: OQRRZRHBPZSJOK-KBNOKHGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  acetylacetate de di-O-isopropylidene-2,3:4,5 β-D fructopyranose 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 2,3:4,5-di-O-isopropylidene-β-D-fructopyranos-1-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
• 作为产物：
  描述：

  果糖二丙酮 、 乙酰乙酸甲酯 反应 18.0h， 以92%的产率得到acetylacetate de di-O-isopropylidene-2,3:4,5 β-D fructopyranose
  参考文献：
  名称：

  Zehani, Sadek; Llauro, Marie-France; Gelbard, Georges, Bulletin de la Societe Chimique de France, 1989, # 1, p. 104 - 113

  摘要：

  DOI：

文献信息

• Natural clays as efficient catalyst for transesterification of β-keto esters with carbohydrate derivatives
  作者：Fernando C. da Silva、Vitor F. Ferreira、Renata S. Rianelli、Wilma C. Perreira

  DOI：10.1016/s0040-4039(01)02388-7

  日期：2002.2

  Smectite, atapulgite and vermiculite clays catalyzed efficiently transesterifications of β-keto esters and carbohydrate derivatives in good to high yields without decomposition of the carbohydrate moieties.

  蒙脱石，凹凸棒石和ver石粘土有效地催化了β-酮酸酯和碳水化合物衍生物的酯交换反应，收率高至高，而没有碳水化合物部分的分解。
• Mild Diazo Transfer Reaction Catalyzed by Modified Clays
  作者：Renata de S. Rianelli、Maria Cecília B. V. de Souza、Vitor F. Ferreira

  DOI：10.1081/scc-120028368

  日期：2004.12.31

  A very mild method for the preparation of various 2-diazo-1,3-carbonyl compounds in the presence of environmentally attractive solid acids such as clays in a heterogeneous manner in moderate to good yield is reported.
• ZEHANI, SADEK;LLAURO, MARIE-FRANCE;GELBARD, GEORGES, BULL. SOC. CHIM. FR.,(1989) N, C. 104-113
  作者：ZEHANI, SADEK、LLAURO, MARIE-FRANCE、GELBARD, GEORGES

  DOI：——

  日期：——
• Zehani, Sadek; Llauro, Marie-France; Gelbard, Georges, Bulletin de la Societe Chimique de France, 1989, # 1, p. 104 - 113
  作者：Zehani, Sadek、Llauro, Marie-France、Gelbard, Georges

  DOI：——

  日期：——
• Asymmetric cyclopropanation with diazoacetates induced by carbohydrate-derived chiral auxiliaries
  作者：Vitor F. Ferreira、Raquel A.C. Leão、Fernando de C. da Silva、Sergio Pinheiro、Paul Lhoste、Denis Sinou

  DOI：10.1016/j.tetasy.2007.04.027

  日期：2007.6

  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.