3-phenyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) thiocarbamide | 121388-66-7

• 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: 3-phenyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) thiocarbamide
• 英文别名: N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N'-phenyl thiourea；N-phenyl-N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiourea；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(phenylcarbamothioylamino)oxan-2-yl]methyl acetate
• CAS: 121388-66-7；71454-45-0
• 化学式: C₂₁H₂₆N₂O₉S
• 分子量: 482.511
• InChiKey: NPAYSBKCNHILNY-OUUBHVDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  171
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-phenyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) thiocarbamide 在 甲醇 、 sodium methylate 作用下， 以86%的产率得到N-(β-D-glucopyranosyl)-N'-phenyl thiourea
  参考文献：
  名称：

  评估制备N-β-d-吡喃葡萄糖基-N'-取代的脲，-硫脲和相关化合物的合成方法。

  摘要：

  O-过乙酰化的N-β-d-吡喃葡萄糖基-N'-酰基脲衍生物的制备在以下条件下形成端基异构体混合物：在ZnCl存在下，酰氯将O-过乙酰化的β-d-吡喃葡萄糖基脲酰化（2）在回流的CHCl（3）中；在室温下，将O-过乙酰化的β-d-吡喃葡萄糖胺加到乙腈中的酰基异氰酸酯上；在回流甲苯中将羧酰胺添加到原位制备的O-过乙酰化的β-d-吡喃葡萄糖基异氰酸酯中。在碱下（NaOMe在rt或以下的MeOH中）或在酸（KHSO（4）或rt在MeOH中的accl）催化的酯交换条件导致O-全乙酰化N-β-d-吡喃葡萄糖基-N'-酰基脲的脱保护N'-酰基部分不可避免的部分裂解。β-d-吡喃葡萄糖基氨基甲酸铵与异氰酸酯的反应，

  DOI：

  10.1016/j.carres.2008.01.045
• 作为产物：
  描述：

  苯基硫脲 在 镍 作用下， 以 乙醇 、 苯 为溶剂， 反应 3.5h， 生成 3-phenyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) thiocarbamide
  参考文献：
  名称：

  Ali, M. Umar; Meshram, H. M.; Paranjpe, M. G., Journal of the Indian Chemical Society, 1985, vol. 62, # 9, p. 666 - 669

  摘要：

  DOI：

文献信息

• Synthesis and Schematic Mechanism of 3-Phenylamino-4-phenyl-5-tetra-O-acetyl-b-Dglucopyranosylimino- 1,2,4-dithiazolidines and Its De-acetylated Nucleoside
  作者：Aruna Hardas、Priti Tayade (Gosavi)

  DOI：10.14233/ajchem.2018.21472

  日期：——

  A systematic synthesis of 3-phenylimino-4-phenyl-5-tetra-O-acetyl-b-D-glucopyranosylimino-1,2,4- dithiazolidine (acetylated glucopyranosylimino nucleoside) from glucose as starting material. The steps included acetylating glucose to glucose penta-acetate (II). Step 2 involves the bromination of glucose penta-acetate (II) to 2,3,4,6 tetra-O-acetyl-a-D-glucopyranosyl bromide (III). In step 3 compound (III) reacted with lead thiocyanate to give 2,3,4,6-tetra-O-acetyl-b-D-glucopyranosyl isothiocyanate (IV). In the step 4 N-phenyl-3-tetra-O-acetyl-b-D-glucopyranosyl isothiocyanate (V) was prepared. In the last step on refluxing compound (V) with N-phenyl S-chloro isothiocarbamoyl chloride to yield acetylated glucopyranosyl nucleoside. Furthermore de-acetylating of acetylated glucopyranosyl nucleoside was carried out to obtain 3-phenylimino-4-phenyl-5-b-D-gluopyranosyl imino 1,2,4-dithiazolidine (de-acetylated glucopyranosylimino nucleoside). The synthesized acetylated glucopyranosylimino nucleoside and deacetylated glucopyranosylimono nucleoside were structurally confirmed by elemental analysis, ultraviolet spectral analysis, infrared spectroscopy, nuclear magnetic resonance spectroscopy and mass spectroscopy.

  从葡萄糖作为起始材料，系统合成了3-苯基亚胺-4-苯基-5-四乙酰基-β-D-葡萄糖吡喃亚胺-1,2,4-二噁烷（乙酰化葡萄糖吡喃亚胺核苷）。步骤包括将葡萄糖乙酰化为葡萄糖五乙酸酯（II）。步骤2涉及将葡萄糖五乙酸酯（II）溴化为2,3,4,6-四乙酰基-α-D-葡萄糖吡喃基溴化物（III）。在步骤3中，化合物（III）与硫氰酸铅反应，生成2,3,4,6-四乙酰基-β-D-葡萄糖吡喃基异硫氰酸酯（IV）。在步骤4中，制备了N-苯基-3-四乙酰基-β-D-葡萄糖吡喃基异硫氰酸酯（V）。在最后一步，复流化合物（V）与N-苯基S-氯异硫脲氯化物反应，得到乙酰化的葡萄糖吡喃核苷。此外，对乙酰化的葡萄糖吡喃核苷进行去乙酰化，获得3-苯基亚胺-4-苯基-5-β-D-葡萄糖吡喃亚胺-1,2,4-二噁烷（去乙酰化的葡萄糖吡喃亚胺核苷）。合成的乙酰化葡萄糖吡喃亚胺核苷和去乙酰化葡萄糖吡喃亚胺核苷通过元素分析、紫外光谱分析、红外光谱、核磁共振谱和质谱进行了结构确认。
• Novel and Efficient Synthesis of 4-Dimethylamino-2-glycosylaminoquinazolines by Cyclodesulfurization of Glycosyl Thioureas with Dimethylcyanamide.
  作者：Yasuo Gama、Isao Shibuya、Masao Shimizu

  DOI：10.1248/cpb.50.1517

  日期：——

  4-Dimethylamino-2-glycosylaminoquinazoline derivatives were synthesized by cyclodesulfurization of N-aryl-N′-glycosyl thioureas with dimethylcyanamide in the presence of silver triflate in good yields.

  在三酸银存在下，通过 N-芳基-N′-糖基硫脲与二甲基氰酰胺的环去硫化反应，合成了 4-二甲基氨基-2-糖基氨基喹唑啉衍生物，产率良好。
• Yadgire, Atul V.; Korpe, Gajanan V.; Deshmukh, Shirish P., E-Journal of Chemistry, 2011, vol. 8, # 4, p. 1614 - 1619
  作者：Yadgire, Atul V.、Korpe, Gajanan V.、Deshmukh, Shirish P.

  DOI：——

  日期：——
• Thiourea linked peracetylated glucopyranosyl–anthraquinone conjugate as reversible ON–OFF receptor for fluoride in acetonitrile
  作者：Sivaiah Areti、Jayshree K. Khedkar、Ramakrishna Chilukula、Chebrolu P. Rao

  DOI：10.1016/j.tetlet.2013.08.008

  日期：2013.10

  A new thiourea linked peracetylated glucopyranosyl-anthraquinone conjugate (L) has been synthesized and characterized. The binding properties of L have been studied with nineteen different anions. The L exhibited selective chromogenic as well as fluorescent chemosensor property toward F- by a similar to 13-fold increase in the emission intensity upon binding with F-. The minimal detection limit for F- is 185 +/- 5 ppb in acetonitrile. Interaction of F- led to a bathochromic shift of 80 nm in the absorption band. An INHIBIT logic gate has been proposed using the output obtained from the fluorescence studies. The structure of the species formed upon the interaction of F- with L has been established by DFT computations. (C) 2013 Elsevier Ltd. All rights reserved.