O-ethyl N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamate | 154446-11-4

• 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: O-ethyl N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamate
• 英文别名: Ethyl N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamate；ethyl-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamate；(tetra-O-acetyl-β-D-glucopyranosyl)-thiocarbamic acid O-ethyl ester；(Tetra-O-acetyl-β-D-glucopyranosyl)-thiocarbamidsaeure-O-aethylester；Tetra-O-acetyl-N-aethoxythiocarbonyl-β-D-glucopyranosylamin；Tetraacetylglucose-thiourethan；2,3,4,6-tetra-O-acetyl-N-(ethoxycarbonothioyl)-beta-D-glucopyranosylamine；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(ethoxycarbothioylamino)oxan-2-yl]methyl acetate
• CAS: 154446-11-4
• 化学式: C₁₇H₂₅NO₁₀S
• 分子量: 435.452
• InChiKey: ZIPCHHGXLBUBHP-IBEHDNSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  168
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  bis[(benzyldimethylamino)chloropalladium(II)] 、 O-ethyl N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamate 以 二氯甲烷 为溶剂， 以95%的产率得到chloro(N,N-dimethylbenzylamine-2-C,N){ethyl-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamate}palladium(II)
  参考文献：
  名称：

  Pill, Thomas; Beck, Wolfgang, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1993, vol. 48, # 11, p. 1461 - 1469

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 乙醇 作用下， 生成 O-ethyl N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamate
  参考文献：
  名称：

  Fischer,E., Chemische Berichte, 1914, vol. 47, p. 1389

  摘要：

  DOI：

文献信息

• Synthesis, antifungal activities, and potential detoxification of N-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)thiocarbamates
  作者：Yaling Zhou、Li Wang、Lixia Han、Fangui Meng、Chunlong Yang

  DOI：10.1016/j.carres.2009.05.008

  日期：2009.7

  A series of N-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)thiocarbamates were synthesized by the reaction of glucosyl isothiocyanates with monohydric and dihydric alcohols, and acetone oxime, using methods of both normal reaction and microwave-assisted synthesis. Antifungal activities of the title compounds were determined with three kinds of plant pathogenic fungi, Fusarium graminearum, Rhizoctoria

  葡萄糖N-（2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基）硫代氨基甲酸酯是通过异硫氰酸葡萄糖基酯与一元和二元醇以及丙酮肟的反应合成的，采用常规方法反应和微波辅助合成。用三种植物病原真菌，禾谷镰刀菌，谷物根瘤菌和球形炭疽菌测定了标题化合物的抗真菌活性。合成的葡萄糖基硫代氨基甲酸酯容易与HgCl（2）反应，生成新型金属有机化合物，双[O-烷基N-（2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基）硫代氨基甲酸酯]汞，收率为80％。硫代氨基甲酸酯与汞的这种强亲和力表明了其在医学或海洋环境排毒中的潜在效用。
• Blanco, Jose L. Jimenez; Barria, Claudio Saitz; Benito, Juan M., Synthesis, 1999, # 11, p. 1907 - 1914
  作者：Blanco, Jose L. Jimenez、Barria, Claudio Saitz、Benito, Juan M.、Mellet, Carmen Ortiz、Fuentes, Jose、Santoyo-Gonzales, Francisco、Fernandez, Jose M. Garcia

  DOI：——

  日期：——
• Mueller; Wilhelms, Chemische Berichte, 1941, vol. 74, p. 698,700
  作者：Mueller、Wilhelms

  DOI：——

  日期：——
• <i>O</i>-Ethyl and<i>O</i>-methyl<i>N</i>-(2,3,4,6-tetra-<i>O</i>-acetyl-β-<scp>D</scp>-glucopyranosyl)thiocarbamate
  作者：Shusheng Zhang、Zhongwei Wang、Ming Li、Kui Jiao、Ibrahim Abdul Razak、S. Shanmuga Sundara Raj、Hoong-Kun Fun

  DOI：10.1107/s0108270101000609

  日期：2001.5.15

  In both the title structures, O-ethyl N-(2,3,4,6-tetra-O-acetyl-beta -D-glucopyranosyl)thiocarbamate, C17H25NO10S, and O-methyl N-(2,3,4,6-tetra-O-acetyl-beta -D-glucopyranosyl)thiocarbamate, C16H23NO10S, the hexopyranosyl ring adopts the C-4(1) conformation. All the ring substituents are in equatorial positions. The acetoxymethyl group is in a gauche-gauche conformation. The S atom is in a synperiplanar conformation, while the C-N-C-O linkage is antiperiplanar. N-H . . .O intermolecular hydrogen bonds link the molecules into infinite chains and these are connected by C-H . . .O interactions.