(1,4,6-tri-O-acetyl-2,3-dideoxy-α-D-mannopyranoso)[2,3-d]oxazolidine-2-thione | 1101121-75-8

• 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: (1,4,6-tri-O-acetyl-2,3-dideoxy-α-D-mannopyranoso)[2,3-d]oxazolidine-2-thione
• 英文别名: [(3aS,4R,6R,7S,7aR)-4,7-diacetyloxy-2-sulfanylidene-3,3a,4,6,7,7a-hexahydropyrano[3,4-d][1,3]oxazol-6-yl]methyl acetate
• CAS: 1101121-75-8
• 化学式: C₁₃H₁₇NO₈S
• 分子量: 347.346
• InChiKey: NQEBNQVRZYEXGH-ROHXPCBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  在 乙烷,三氯氟- 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以74 mg的产率得到(1,4,6-tri-O-acetyl-2,3-dideoxy-α-D-mannopyranoso)[2,3-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