[(3aR,5R,6S,6aR)-5-[(1S)-2-(diethylcarbamothioylsulfanyl)-1-hydroxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] N,N-diethylcarbamate | 187930-04-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(3aR,5R,6S,6aR)-5-[(1S)-2-(diethylcarbamothioylsulfanyl)-1-hydroxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] N,N-diethylcarbamate
• CAS: 187930-04-7
• 化学式: C₁₉H₃₄N₂O₆S₂
• 分子量: 450.621
• InChiKey: UPEPOBOWMFBCII-IBEHDNSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(3aR,5R,6S,6aR)-5-[(1S)-2-(diethylcarbamothioylsulfanyl)-1-hydroxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] 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70%的产率得到Diethyl-carbamic acid (2S,3S,4S,5R)-2-diethylthiocarbamoylsulfanylmethyl-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：

  [(3aR,5R,6S,6aR)-5-[(1R)-1,2-dihydroxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] N,N-diethylcarbamate 以 吡啶 、 丙酮 、 甲苯 为溶剂， 反应 1.0h， 生成 [(3aR,5R,6S,6aR)-5-[(1S)-2-(diethylcarbamothioylsulfanyl)-1-hydroxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] 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

文献信息

• Synthesis of Bis(Carbamoyl Ester) Derivatives of D-Glucose as Antifungal Products
  作者：Christophe Len、Denis Postel、Gino Ronco、Pierre Villa

  DOI：10.1080/07328309708005735

  日期：1997.9

  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.