1,3-dideoxy-5,6:7,8-di-O-isopropylidene-β-D-manno-non-2,5-diulo-5,9-pyranose | 405143-56-8

• 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: 1,3-dideoxy-5,6:7,8-di-O-isopropylidene-β-D-manno-non-2,5-diulo-5,9-pyranose
• 英文别名: (4R)-4-hydroxy-4-[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]butan-2-one
• CAS: 405143-56-8
• 化学式: C₁₅H₂₄O₇
• 分子量: 316.351
• InChiKey: NSVPXRNDYOCINS-CYRTVHNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 1,3-dideoxy-5,6:7,8-di-O-isopropylidene-β-D-manno-non-2,5-diulo-5,9-pyranose 在 sodium hypobromide 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 2.5h， 生成 methyl 2-deoxy-4,5:6,7-di-O-isopropylidene-β-D-manno-oct-4-ulo-4,8-pyranosonate
  参考文献：
  名称：

  Highly stereocontrolled alkylation of protected ‘diacetone hexulose aldehydes’

  摘要：

  Claisen Schmidt aldol condensation (with acetone, catalysed by L- and D-proline), Knoevenagel reaction with acetoacetic acid and the modified Reformatsky reaction with bromoacetone of the 'diacetone hexulose aldehydes' 2 and 7 gave the corresponding beta -hydroxyketones 3 4 and 8-9 as well as the (E)-alpha,beta -enones 5 and 10, respectively. The highest chemo- and stereoselectivities were obtained with the Knoevenagel procedure using L-proline as the catalyst. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00488-8
• 作为产物：
  描述：

  果糖二丙酮 在 N-甲基吲哚酮 、 四丙基高钌酸铵 、 4 Angstroem MS 、 碘 、 锌 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 1,3-dideoxy-5,6:7,8-di-O-isopropylidene-β-D-manno-non-2,5-diulo-5,9-pyranose
  参考文献：
  名称：

  Highly stereocontrolled alkylation of protected ‘diacetone hexulose aldehydes’

  摘要：

  Claisen Schmidt aldol condensation (with acetone, catalysed by L- and D-proline), Knoevenagel reaction with acetoacetic acid and the modified Reformatsky reaction with bromoacetone of the 'diacetone hexulose aldehydes' 2 and 7 gave the corresponding beta -hydroxyketones 3 4 and 8-9 as well as the (E)-alpha,beta -enones 5 and 10, respectively. The highest chemo- and stereoselectivities were obtained with the Knoevenagel procedure using L-proline as the catalyst. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00488-8

文献信息

• Highly stereocontrolled alkylation of protected ‘diacetone hexulose aldehydes’
  作者：Isidoro Izquierdo、Marı́a T. Plaza、Rafael Robles、Antonio J. Mota、Francisco Franco

  DOI：10.1016/s0957-4166(01)00488-8

  日期：2001.10

  Claisen Schmidt aldol condensation (with acetone, catalysed by L- and D-proline), Knoevenagel reaction with acetoacetic acid and the modified Reformatsky reaction with bromoacetone of the 'diacetone hexulose aldehydes' 2 and 7 gave the corresponding beta -hydroxyketones 3 4 and 8-9 as well as the (E)-alpha,beta -enones 5 and 10, respectively. The highest chemo- and stereoselectivities were obtained with the Knoevenagel procedure using L-proline as the catalyst. (C) 2001 Elsevier Science Ltd. All rights reserved.