3,6-dideoxybis[3,6-S-(N,N-diethyldithiocarbamoyl)]-1,2-O-isopropylidene-α-D-glucofuranose | 187929-96-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 3,6-dideoxybis[3,6-S-(N,N-diethyldithiocarbamoyl)]-1,2-O-isopropylidene-α-D-glucofuranose
• 英文别名: [(2S)-2-[(3aR,5R,6S,6aS)-6-(diethylcarbamothioylsulfanyl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl] N,N-diethylcarbamodithioate
• CAS: 187929-96-0
• 化学式: C₁₉H₃₄N₂O₄S₄
• 分子量: 482.754
• InChiKey: CDTBELAHBKQOHE-DGXTUMSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 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：
  54.4
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3,6-dideoxybis[3,6-S-(N,N-diethyldithiocarbamoyl)]-1,2-O-isopropylidene-α-D-glucofuranose 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 以50%的产率得到3,6-dideoxybis[3,6-S-(N,N-diethyldithiocarbamoyl)]-D-glucopyranose
  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-S-(N,N-diethylthiocarbamoyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 盐酸 作用下， 以 1,4-二氧六环 、 吡啶 、 水 、 丙酮 、 甲苯 为溶剂， 反应 53.0h， 生成 3,6-dideoxybis[3,6-S-(N,N-diethyldithiocarbamoyl)]-1,2-O-isopropylidene-α-D-glucofuranose
  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 and Antifungal Activity of Novel Bisdithiocarbamate Derivatives of Carbohydrates against <i>Fusarium oxysporum</i> f. sp. <i>l</i><i>ini</i>
  作者：Catherine Rafin、Etienne Veignie、Michel Sancholle、Denis Postel、Christophe Len、Pierre Villa、Gino Ronco

  DOI：10.1021/jf0003698

  日期：2000.11.1

  from glycerol or D-glucose with two N,N-diethyldithiocarbamoyl groups and a series of bisdithiocarbamic esters having a ketone or an alkyl ester have been synthesized. The in vitro activity of these new compounds was evaluated against Fusarium oxysporum f. sp. lini. Some of the compounds [bis[1,3-S-(N,N-diethyldithiocarbamoyl)]-1, 3-dideoxyglycerol) and diethyl N,N'-(1,3-dideoxyglycer-1, 3-diyl)bis(dithiocarbamate)]

  合成了具有衍生自具有两个N，N-二乙基二硫代氨基甲酰基的甘油或D-葡萄糖的碳水化合物部分的新型氨基甲酸酯和一系列具有酮或烷基酯的双二硫代氨基甲酸酯。评估了这些新化合物对尖孢镰刀菌f的体外活性。sp。莉妮。一些化合物[双[1,3-S-（N，N-二乙基二硫代氨基甲酰基）]-1，3-二脱氧甘油）和二乙基N，N'-（1,3-二脱氧甘油-1，3-二基）双（ （二硫代氨基甲酸酯）]分别比市售N，N-二乙基二硫代氨基甲酸钠盐和Maneb更具抑制菌丝体生长的活性。讨论了这些新化合物的结构活性。