3-O-(N,N-diethylcarbamoyl)-1,2:5,6-di-O-isopropylidene-α-D-glucose | 85141-64-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-(N,N-diethylcarbamoyl)-1,2:5,6-di-O-isopropylidene-α-D-glucose
• 英文别名: [(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] N,N-diethylcarbamate
• CAS: 85141-64-6
• 化学式: C₁₇H₂₉NO₇
• 分子量: 359.42
• InChiKey: MXMBIOKLTNGVRS-RKQHYHRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  75.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  N,N-二乙基氯甲酰胺 、 双丙酮葡萄糖 在 氢氧化钾 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 0.17h， 以95%的产率得到3-O-(N,N-diethylcarbamoyl)-1,2:5,6-di-O-isopropylidene-α-D-glucose
  参考文献：
  名称：

  单糖和 ITOLS 的二硫、硫和氨基甲酸酯衍生物的合成

  摘要：

  摘要 O-异亚丙基保护的单糖和醇的区域特异性氨基甲酰化得到了大范围的新型氨基甲酰基、硫代氨基甲酰基和二硫代氨基甲酰基酯。这些完全、部分和未受保护的碳水化合物同时具有可调节的亲水特性和潜在的生物学特性。一些氨基甲酸酯通过核磁共振谱显示出ZE异构特征；硫代氨基甲酸酯的旋转能垒高于相应的氨基甲酸酯。

  DOI：

  10.1080/10426509808032452

文献信息

• Copeland, Christopher; Stick, Robert V., Australian Journal of Chemistry, 1982, vol. 35, # 12, p. 2541 - 2546
  作者：Copeland, Christopher、Stick, Robert V.

  DOI：——

  日期：——
• McAdam, David P.; Stick, Robert V., Australian Journal of Chemistry, 1988, vol. 41, # 4, p. 563 - 573
  作者：McAdam, David P.、Stick, Robert V.

  DOI：——

  日期：——
• MCADAM, DAVID P.;STICK, ROBERT V., AUSTRAL. J. CHEM., 41,(1988) N 4, C. 563-573
  作者：MCADAM, DAVID P.、STICK, ROBERT V.

  DOI：——

  日期：——
• SYNTHESIS OF DITHIO-, THIO-AND CARBAMOYL ESTER DERIVATIVES OF MONOSACCHARIDES AND ITOLS
  作者：Christophe Len、Denis Postel、Gino Ronco、Pierre Villa

  DOI：10.1080/10426509808032452

  日期：1998.1

  unprotected carbohydrates possess both modulable hydrophilic character and potential biological properties. Some carbamoyl esters showed, by NMR spectroscopy, characteristics of Z-E isomerism; the rotational energy barrier was higher for the thiocarbamates than for the corresponding carbamates.

  摘要 O-异亚丙基保护的单糖和醇的区域特异性氨基甲酰化得到了大范围的新型氨基甲酰基、硫代氨基甲酰基和二硫代氨基甲酰基酯。这些完全、部分和未受保护的碳水化合物同时具有可调节的亲水特性和潜在的生物学特性。一些氨基甲酸酯通过核磁共振谱显示出ZE异构特征；硫代氨基甲酸酯的旋转能垒高于相应的氨基甲酸酯。
• 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.