S-(β-D-glucopyranosyl) N,N-diethyldithiocarbamate | 19200-30-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: S-(β-D-glucopyranosyl) N,N-diethyldithiocarbamate
• 英文别名: N,N-diethyl β-D-glucopyranosyl dithiocarbamate；N,N-diethyl β-galactopyranosyl dithiocarbamate；β-D-Glucopyranosyl-N,N-diaethyl-dithiocarbamat；S-(beta-D-Glucopyranosyl)-N,N-diethyldithiocarbamate；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] N,N-diethylcarbamodithioate
• CAS: 19200-30-7
• 化学式: C₁₁H₂₁NO₅S₂
• 分子量: 311.423
• InChiKey: NZZCKKHDYOKHCF-SPFKKGSWSA-N

物化性质

• 熔点：
  121-122 °C(Solv: isopropanol (67-63-0))
• 沸点：
  503.8±60.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  151
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  S-(β-D-glucopyranosyl) N,N-diethyldithiocarbamate 、 烯丙基三丁基锡 在 偶氮二异丁腈 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以67%的产率得到1-(α-D-galactopyranosyl)-2-propene
  参考文献：
  名称：

  一种通过糖基二硫代氨基甲酸酯合成 C-糖苷的无保护基团方法

  摘要：

  通过一步可制备的糖基二硫代氨基甲酸酯 (GDTC) 实现了自由基C-糖基化的第一个无保护/去保护过程。在温和的反应条件下，成功地进行了未受保护的GDTCs的Giese型反应和自由基烯丙基化反应，立体选择性地获得了相应的α -C-糖苷。

  DOI：

  10.1039/d1ob00311a
• 作为产物：
  描述：

  S-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl) N,N-diethyldithiocarbamate 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以72%的产率得到S-(β-D-glucopyranosyl) N,N-diethyldithiocarbamate
  参考文献：
  名称：

  Sugar-Linked Dithiocarbamates as Modulators of Metabolic and Genotoxic Properties of N-Nitroso Compounds

  摘要：

  A series of putative anticarcinogenic and antimutagenic compounds was synthesized on the basis of tetraethylthiuram disulfide (disulfiram) and its metabolite, diethyldithiocarbamate (DDTC). Diallyldithiocarbamate was synthesized in order to combine the anticarcinogenic properties of diallyl sulfide, a known inhibitor of chemical carcinogenesis from Allium species, and those of DDTC. Several sugar-linked dithiocarbamates (SDTCs) were prepared using glucose, cellobiose, and lactose as glycosyl donors and DDTC and diallyldithiocarbamate as accepters. All the S-glycoside bonds of SDTCs were very stable under physiological conditions in vitro. At low nitrosamine concentrations, glucose-DDTC inhibited microsomal nitrosamine dealkylases in vitro. In vivo these enzymes were also inhibited 4 h after ip administration of glucose-DDTC or lactose-DDTC to rats (1.7 mmol/kg); after 24 h, the values had returned to control levels. Glucose-DDTC induced the activity of glutathione-related enzymes. Concomitant treatment of rats with glucose-DDTC and N-nitrosodiethylamine (NDEA) led to a depression of the oxidative metabolism of [C-14]NDEA to (CO2)-C-14 but increased the elimination of unchanged [C-14]NDEA in the urine. Furthermore, glucose-DDTC totally inhibited the formation of DNA single-strand breaks induced by NDEA. All these effects may contribute to possible antimutagenic and anticarcinogenic actions of the dithiocarbamates investigated.

  DOI：

  10.1021/jm00045a021

文献信息

• Protection-free synthesis of glycosyl dithiocarbamates in aqueous media by using 2-chloroimidazolinium reagent
  作者：Gefei Li、Masato Noguchi、Haruka Kashiwagura、Yuuki Tanaka、Kazunari Serizawa、Shin-ichiro Shoda

  DOI：10.1016/j.tetlet.2016.06.106

  日期：2016.8

  have been synthesized directly from the corresponding unprotected sugars and dithiocarbamate salts in good yields by using 2-chloro-1,3-dimethylimidazolinium chloride (DMC) as condensing agent in aqueous media. The three-component one-pot synthesis of GDTCs starting from unprotected sugars, carbon disulfide, and secondary amines has also been successfully demonstrated. This is the first report on the

  使用2-氯-1,3-二甲基咪唑啉鎓氯化物（DMC）作为缩合剂在水性介质中，可以直接从相应的未保护糖和二硫代氨基甲酸盐以高收率直接合成糖基二硫代氨基甲酸酯（GDTC）。还已经成功地证明了从未保护的糖，二硫化碳和仲胺开始的三组分一锅法合成GDTC。这是有关不使用任何保护基团由未保护的糖直接合成GDTC的首次报道。
• Sugar-Linked Dithiocarbamates as Modulators of Metabolic and Genotoxic Properties of N-Nitroso Compounds
  作者：Byung-Hoon Lee、Barbara Bertram、Peter Schmezer、Norbert Frank、Manfred Wiessler

  DOI：10.1021/jm00045a021

  日期：1994.9

  A series of putative anticarcinogenic and antimutagenic compounds was synthesized on the basis of tetraethylthiuram disulfide (disulfiram) and its metabolite, diethyldithiocarbamate (DDTC). Diallyldithiocarbamate was synthesized in order to combine the anticarcinogenic properties of diallyl sulfide, a known inhibitor of chemical carcinogenesis from Allium species, and those of DDTC. Several sugar-linked dithiocarbamates (SDTCs) were prepared using glucose, cellobiose, and lactose as glycosyl donors and DDTC and diallyldithiocarbamate as accepters. All the S-glycoside bonds of SDTCs were very stable under physiological conditions in vitro. At low nitrosamine concentrations, glucose-DDTC inhibited microsomal nitrosamine dealkylases in vitro. In vivo these enzymes were also inhibited 4 h after ip administration of glucose-DDTC or lactose-DDTC to rats (1.7 mmol/kg); after 24 h, the values had returned to control levels. Glucose-DDTC induced the activity of glutathione-related enzymes. Concomitant treatment of rats with glucose-DDTC and N-nitrosodiethylamine (NDEA) led to a depression of the oxidative metabolism of [C-14]NDEA to (CO2)-C-14 but increased the elimination of unchanged [C-14]NDEA in the urine. Furthermore, glucose-DDTC totally inhibited the formation of DNA single-strand breaks induced by NDEA. All these effects may contribute to possible antimutagenic and anticarcinogenic actions of the dithiocarbamates investigated.
• A protecting group–free approach for synthesizing <i>C</i>-glycosides through glycosyl dithiocarbamates
  作者：Gefei Li、Masato Noguchi、Genki Arisaka、Yuuki Tanaka、Shin-ichiro Shoda

  DOI：10.1039/d1ob00311a

  日期：——

  The first protection/deprotection-free process for radical C-glycosylation has been achieved through one-step preparable glycosyl dithiocarbamates (GDTCs). The Giese-type reaction and radical allylation of unprotected GDTCs were successfully performed to obtain the corresponding α-C-glycosides stereoselectively under mild reaction conditions.

  通过一步可制备的糖基二硫代氨基甲酸酯 (GDTC) 实现了自由基C-糖基化的第一个无保护/去保护过程。在温和的反应条件下，成功地进行了未受保护的GDTCs的Giese型反应和自由基烯丙基化反应，立体选择性地获得了相应的α -C-糖苷。