[(2R)-2-[(3aR,5R,6S,6aR)-6-(diethylcarbamoyloxy)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl] N,N-diethylcarbamate | 187929-98-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R)-2-[(3aR,5R,6S,6aR)-6-(diethylcarbamoyloxy)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl] N,N-diethylcarbamate
• CAS: 187929-98-2
• 化学式: C₁₉H₃₄N₂O₈
• 分子量: 418.488
• InChiKey: IGZQZHFWEYAVEB-IBEHDNSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  107.0
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  [(2R)-2-[(3aR,5R,6S,6aR)-6-(diethylcarbamoyloxy)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl] N,N-diethylcarbamate 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 以69%的产率得到Diethyl-carbamic acid (2R,3R,4S,5R)-2-diethylcarbamoyloxymethyl-3,5,6-trihydroxy-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis of Bis(Carbamoyl Ester) Derivatives of D-Glucose as Antifungal Products

  摘要：

  Regiospecific carbamoylation of di-O-isopropylidene protected D-glucose gave a series of carbamoyl, thiocarbamoyl and dithiocarbamoyl esters at the C-3 secondary site. These were partially and fully deprotected to give two series of derivatives such that a choice of the extent of hydrophilic character could be made. The partially protected products were further derivatized regioselectively with a second carbamoyl, thiocarbamoyl or dithiocarbamoyl group at the C-6 primary site. We also report on antifungal properties of some of those compounds.

  DOI：

  10.1080/07328309708005735
• 作为产物：
  描述：

  3-O-(N,N-diethylcarbamoyl)-1,2:5,6-di-O-isopropylidene-α-D-glucose 在 盐酸 、 氢氧化钾 作用下， 以 1,4-二氧六环 、 水 、 甲苯 为溶剂， 反应 2.93h， 生成 [(2R)-2-[(3aR,5R,6S,6aR)-6-(diethylcarbamoyloxy)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl] N,N-diethylcarbamate
  参考文献：
  名称：

  Synthesis of Bis(Carbamoyl Ester) Derivatives of D-Glucose as Antifungal Products

  摘要：

  Regiospecific carbamoylation of di-O-isopropylidene protected D-glucose gave a series of carbamoyl, thiocarbamoyl and dithiocarbamoyl esters at the C-3 secondary site. These were partially and fully deprotected to give two series of derivatives such that a choice of the extent of hydrophilic character could be made. The partially protected products were further derivatized regioselectively with a second carbamoyl, thiocarbamoyl or dithiocarbamoyl group at the C-6 primary site. We also report on antifungal properties of some of those compounds.

  DOI：

  10.1080/07328309708005735