5-azido-3-O-tert-butyldimethylsilyl-7-O-tert-butyldiphenylsilyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco-hepto-1,4-furanose | 876405-54-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-azido-3-O-tert-butyldimethylsilyl-7-O-tert-butyldiphenylsilyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco-hepto-1,4-furanose
• CAS: 876405-54-8
• 化学式: C₃₂H₄₉N₃O₅Si₂
• 分子量: 611.929
• InChiKey: BIJXIRVRAPULRR-XYPQWYOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  42.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  94.91
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-azido-3-O-tert-butyldimethylsilyl-7-O-tert-butyldiphenylsilyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco-hepto-1,4-furanose 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以88%的产率得到(3aR,5R,6S,6aR)-5-((R)-1-Azido-3-hydroxy-propyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol
  参考文献：
  名称：

  Diastereoselective syntheses of 1-deoxyhomonojirimycin and two new 1,5,6-trideoxy-1,5-iminoheptitols with d-allo- and l-talo-configuration

  摘要：

  The synthesis of 1-deoxyhomonojirimycin 2, as well as two new diastereomers, namely 1,5,6-trideoxy-1,5-imino-D-allo-heptitol 3 and 1,5,6-trideoxy-1,5-imino-L-talo-heptitol 4, is described. Compound 2 was obtained from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose-while 3 and 4 were obtained from 1, 2:5,6-di-O-isopropylidene-alpha-D-allofuranose. These compounds were transformed in a few steps to the corresponding beta-ketoesters 12 and 18, respectively, which were hydrogenated diastereoselectively in the presence of chiral ruthenium complexes with total control of the C-5 stereogenic centre. The resulting beta-hydroxyesters 13, 19a and 19b are key intermediates for the syntheses of the 1,5,6-trideoxy-1,5-iminoheptitols 2, 3 and 4, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.022
• 作为产物：
  描述：

  3-O-[(t-butyl)dimethylsilyl]-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 吡啶 、 chromium(VI) oxide 、 4-二甲氨基吡啶 、 sodium periodate 、 lithium aluminium tetrahydride 、 sodium azide 、 [(R)-BINAP]RuBr₂ 、 硫酸 、 氢气 、 溶剂黄146 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 20.0~130.0 ℃ 、101.33 kPa 条件下， 反应 124.0h， 生成 5-azido-3-O-tert-butyldimethylsilyl-7-O-tert-butyldiphenylsilyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco-hepto-1,4-furanose
  参考文献：
  名称：

  Diastereoselective syntheses of 1-deoxyhomonojirimycin and two new 1,5,6-trideoxy-1,5-iminoheptitols with d-allo- and l-talo-configuration

  摘要：

  The synthesis of 1-deoxyhomonojirimycin 2, as well as two new diastereomers, namely 1,5,6-trideoxy-1,5-imino-D-allo-heptitol 3 and 1,5,6-trideoxy-1,5-imino-L-talo-heptitol 4, is described. Compound 2 was obtained from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose-while 3 and 4 were obtained from 1, 2:5,6-di-O-isopropylidene-alpha-D-allofuranose. These compounds were transformed in a few steps to the corresponding beta-ketoesters 12 and 18, respectively, which were hydrogenated diastereoselectively in the presence of chiral ruthenium complexes with total control of the C-5 stereogenic centre. The resulting beta-hydroxyesters 13, 19a and 19b are key intermediates for the syntheses of the 1,5,6-trideoxy-1,5-iminoheptitols 2, 3 and 4, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.022