Tetraacetyl-μ-thioglucoxazolin | 97618-32-1

• 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: Tetraacetyl-μ-thioglucoxazolin
• 英文别名: N-acetyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[2,1-d]oxazolidine-2-thione；(3aR)-6t,7c-diacetoxy-5c-acetoxymethyl-1-acetyl-(3ar,7ac)-tetrahydro-pyrano[3,2-d]oxazole-2-thione；O³,O⁴,O⁶-triacetyl-2-acetylamino-N,O¹-thiocarbonyl-α-D-2-deoxy-glucopyranose；[(3aR,5R,6S,7R,7aR)-1-acetyl-6,7-diacetyloxy-2-sulfanylidene-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]oxazol-5-yl]methyl acetate
• CAS: 97618-32-1
• 化学式: C₁₅H₁₉NO₉S
• 分子量: 389.383
• InChiKey: SVYBXVZXYSPHJT-DHGKCCLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Tetraacetyl-μ-thioglucoxazolin 在 乙烷,三氯氟- 作用下， 以 乙醇 为溶剂， 反应 13.0h， 以78%的产率得到(3,4,6-tri-O-acetyl-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
• 作为产物：
  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