(1,2-dideoxy-α-D-glucopyranoso)[2,1-d]oxazolidine-2-thione | 91982-19-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1,2-dideoxy-α-D-glucopyranoso)[2,1-d]oxazolidine-2-thione
• 英文别名: (3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-1,3a,5,6,7,7a-hexahydropyrano[3,2-d][1,3]oxazole-2-thione
• CAS: 91982-19-3
• 化学式: C₇H₁₁NO₅S
• 分子量: 221.234
• InChiKey: CRGLIKOYHHLORA-QZABAPFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (1,2-dideoxy-α-D-glucopyranoso)[2,1-d]oxazolidine-2-thione 在 吡啶 作用下， 生成 Tetraacetyl-μ-thioglucoxazolin
  参考文献：
  名称：

  cis-Fused bicyclic sugar thiocarbamates. Reactivity towards amines

  摘要：

  1,2-cis-Fused bicyclic sugar thiocarbamates of gluco, and manno configurations have been prepared by treatment of the corresponding O-unprotected amino Sugars and glycopyranosyl amines with thiophosgene. The reactivity of these Compounds towards amines has been studied in order to determine whether these Compounds could act as latent isothiocyanates; it is shown that 1,2-cis-fused bicyclic Sugar thiocarbamates are more stable than their trans analogues, and are]lot transformed into thioureas upon treatment with amines. An unprecedented isomerization of a peracetylated glucopyranoso[2,1-d] oxazolidine-2-thione into a glucopyranoso[2,1-d]thiazolidin-2-one in DMF is also reported. The structure of this thiazolidin-2-one was confirmed by X-ray crystallography. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.09.093
• 作为产物：
  描述：

  硫光气 、 2-氨基-2-脱氧葡萄糖盐酸盐 在 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.5h， 以77%的产率得到(1,2-dideoxy-α-D-glucopyranoso)[2,1-d]oxazolidine-2-thione
  参考文献：
  名称：

  cis-Fused bicyclic sugar thiocarbamates. Reactivity towards amines

  摘要：

  1,2-cis-Fused bicyclic sugar thiocarbamates of gluco, and manno configurations have been prepared by treatment of the corresponding O-unprotected amino Sugars and glycopyranosyl amines with thiophosgene. The reactivity of these Compounds towards amines has been studied in order to determine whether these Compounds could act as latent isothiocyanates; it is shown that 1,2-cis-fused bicyclic Sugar thiocarbamates are more stable than their trans analogues, and are]lot transformed into thioureas upon treatment with amines. An unprecedented isomerization of a peracetylated glucopyranoso[2,1-d] oxazolidine-2-thione into a glucopyranoso[2,1-d]thiazolidin-2-one in DMF is also reported. The structure of this thiazolidin-2-one was confirmed by X-ray crystallography. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.09.093

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。
• cis-Fused bicyclic sugar thiocarbamates. Reactivity towards amines
  作者：Óscar López、Encarnación Zafra、Inés Maya、José Fuentes、Ma Jesús Diánez、Ma Dolores Estrada、Simeón Pérez-Garrido、José G. Fernández-Bolaños

  DOI：10.1016/j.tet.2008.09.093

  日期：2008.12

  1,2-cis-Fused bicyclic sugar thiocarbamates of gluco, and manno configurations have been prepared by treatment of the corresponding O-unprotected amino Sugars and glycopyranosyl amines with thiophosgene. The reactivity of these Compounds towards amines has been studied in order to determine whether these Compounds could act as latent isothiocyanates; it is shown that 1,2-cis-fused bicyclic Sugar thiocarbamates are more stable than their trans analogues, and are]lot transformed into thioureas upon treatment with amines. An unprecedented isomerization of a peracetylated glucopyranoso[2,1-d] oxazolidine-2-thione into a glucopyranoso[2,1-d]thiazolidin-2-one in DMF is also reported. The structure of this thiazolidin-2-one was confirmed by X-ray crystallography. (C) 2008 Elsevier Ltd. All rights reserved.