S-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl) N,N-diethyldithiocarbamate | 19200-29-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: S-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl) N,N-diethyldithiocarbamate
• 英文别名: S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N,N-diethyldithiocarbamate；2,3,4,6-tetra-O-acetyl-1-S-[(diethylamino)carbothioyl]-1-thiohexopyranose；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(diethylcarbamothioylsulfanyl)oxan-2-yl]methyl acetate
• CAS: 19200-29-4
• 化学式: C₁₉H₂₉NO₉S₂
• 分子量: 479.573
• InChiKey: CAKBNRXDTOJZKI-SFFUCWETSA-N

物化性质

• 熔点：
  83-85 °C(Solv: ethanol (64-17-5))
• 沸点：
  527.3±60.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  175
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  sodium N,N-diethyldithiocarbamate 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 以 丙酮 为溶剂， 反应 1.0h， 以99%的产率得到S-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl) N,N-diethyldithiocarbamate
  参考文献：
  名称：

  掩蔽的巯基糖：S-Glycopyranosyl-N-单烷基二硫代氨基甲酸酯的化学行为和合成应用

  摘要：

  S- glycopyranosyl- N的化学行为研究和合成开发了作为掩蔽的1-糖基硫醇的-单烷基二硫代氨基甲酸酯（DTC），可通过1-卤代糖与伯胺的二硫代氨基甲酸酯盐的亲核置换轻松制备。这种行为依赖于氨基甲酸酯功能性质子的抽象，该质子允许受控地获取硫醇盐糖中间体。当允许较长的反应时间时，用作试剂的DTC盐的基本特征会导致硫醇盐在原位演化为对称的二糖基二硫化物（DGDS）。或者，可以通过用分离的异头糖基DTC的外部碱处理来有效地获得硫醇盐功能的受控解掩蔽，当使用短的反应时间时，其形成很普遍。以这种方式，建立了制备对称DGDS的第二种方法，以及任何亲电底物S-糖基化的化学方法。这最后一种策略在制备硫代糖基乙烯基砜，硫代二糖和S连接的同价和异二价新糖缀合物中的应用被描述为糖DTC在任何共价的化学情况下具有巨大潜力的概念证明。需要附加巯基糖。还描述了对某些二价硫酸糖体系的生物学功能的评估。和S-

  DOI：

  10.1002/asia.201301270

文献信息

• Radical-mediated reduction of the dithiocarbamate group under tin-free conditions
  作者：Claire McMaster、Robert N. Bream、Richard S. Grainger

  DOI：10.1039/c2ob25434d

  日期：——

  desulfurisation of dithiocarbamates is conveniently achieved using H3PO2–Et3N–ACCN in refluxing dioxane. Fused and spirocyclic β-lactams, prepared through 4-exo trig carbamoyl radical cyclisation–dithiocarbamate group transfer reactions, are reduced without fragmentation of the strained 4-membered ring. Diethyl tetraacetyl-D-glucopyranosyl dithiocarbamate is selectively reduced with or without acyloxy group migration

  使用H 3 PO 2 -Et 3 N-ACCN在回流中方便地实现二硫代氨基甲酸酯的还原脱硫二恶烷。通过4- exo trig氨基甲酰基自由基环化反应-二硫代氨基甲酸酯基团转移反应制得的熔融和螺环β-内酰胺可在不断裂的四元环断裂的情况下被还原。二乙基四乙酰基-D-吡喃葡萄糖基二硫代氨基甲酸酯取决于反应条件和还原剂的选择，在有或没有酰氧基迁移的情况下选择性地还原Aβ。对于涉及亲核基团中间体的系统，可以观察到从D 3 PO 2 -Et 3 N引入氘，但对于通过酰氧基在葡萄糖衍生物上迁移获得的亲电子基团，则观察不到这种情况。