N,N-diethyl-5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-L-glycero-α-D-gluco-heptofuranuronamide | 1423780-03-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N-diethyl-5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-L-glycero-α-D-gluco-heptofuranuronamide
• 英文别名: (2R,3S)-3-[(3aR,5S,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-N,N-diethyloxirane-2-carboxamide
• CAS: 1423780-03-3
• 化学式: C₂₁H₂₉NO₆
• 分子量: 391.464
• InChiKey: FRKGZAUZNZGXEB-RJENKUHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  69.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-L-glycero-α-D-gluco-heptofuranuronamide 在 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 N,N-diethyl-5,6-anhydro-1,2-O-isopropylidene-L-glycero-α-D-gluco-heptofuranuronamide
  参考文献：
  名称：

  Regioselective epoxide opening of epoxyamides derived from d-glucose. Cyclization approaches to azepanes

  摘要：

  Epoxyamides obtained from n-glucose have been evaluated as tools to obtain polyhydroxyazepanes. The stereoselectivity in formation of the epoxyamides was proven to be dependent of the protecting group. The conversion of epoxyamides into epoxyalcohols was necessary to obtain polyhydroxyazepanes, because the direct cyclization of 2-N-amides to azepanecarboxamides was unsuccessful from derivatives obtained from n-glucose. Epoxyamides and epoxyalcohols were regioselectively (alpha) opened by nitrogen nucleophiles. Reduction of diethyl epoxyamide by catalytic transfer hydrogenation gave the alpha deoxy product. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.12.005
• 作为产物：
  描述：

  (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 在 sodium periodate 、 silica gel 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 N,N-diethyl-5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-L-glycero-α-D-gluco-heptofuranuronamide
  参考文献：
  名称：

  Regioselective epoxide opening of epoxyamides derived from d-glucose. Cyclization approaches to azepanes

  摘要：

  Epoxyamides obtained from n-glucose have been evaluated as tools to obtain polyhydroxyazepanes. The stereoselectivity in formation of the epoxyamides was proven to be dependent of the protecting group. The conversion of epoxyamides into epoxyalcohols was necessary to obtain polyhydroxyazepanes, because the direct cyclization of 2-N-amides to azepanecarboxamides was unsuccessful from derivatives obtained from n-glucose. Epoxyamides and epoxyalcohols were regioselectively (alpha) opened by nitrogen nucleophiles. Reduction of diethyl epoxyamide by catalytic transfer hydrogenation gave the alpha deoxy product. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.12.005

文献信息

• Regioselective epoxide opening of epoxyamides derived from d-glucose. Cyclization approaches to azepanes
  作者：Noe Oña、Antonio Romero-Carrasco、M. Soledad Pino-González

  DOI：10.1016/j.tetasy.2012.12.005

  日期：2013.2

  Epoxyamides obtained from n-glucose have been evaluated as tools to obtain polyhydroxyazepanes. The stereoselectivity in formation of the epoxyamides was proven to be dependent of the protecting group. The conversion of epoxyamides into epoxyalcohols was necessary to obtain polyhydroxyazepanes, because the direct cyclization of 2-N-amides to azepanecarboxamides was unsuccessful from derivatives obtained from n-glucose. Epoxyamides and epoxyalcohols were regioselectively (alpha) opened by nitrogen nucleophiles. Reduction of diethyl epoxyamide by catalytic transfer hydrogenation gave the alpha deoxy product. (C) 2012 Elsevier Ltd. All rights reserved.