(3R)-3-acetylamino-4-one-6,7-dihydro-(1',2'-dideoxy-β-D-glucopyranoso)[2',1'-f]-1,5-thiazepane | 949886-08-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R)-3-acetylamino-4-one-6,7-dihydro-(1',2'-dideoxy-β-D-glucopyranoso)[2',1'-f]-1,5-thiazepane
• 英文别名: N-[(3R,5aS,7R,8S,9R,9aR)-8,9-dihydroxy-7-(hydroxymethyl)-2-oxo-1,3,4,5a,7,8,9,9a-octahydropyrano[2,3-b][1,4]thiazepin-3-yl]acetamide
• CAS: 949886-08-2
• 化学式: C₁₁H₁₈N₂O₆S
• 分子量: 306.34
• InChiKey: QPOJJZLMPUXXSN-PFQGKNLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  153
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3R)-3-acetylamino-4-one-6,7-dihydro-(1',2'-dideoxy-β-D-glucopyranoso)[2',1'-f]-1,5-thiazepane 、 乙酸酐 在 吡啶 作用下， 以320 mg的产率得到(3R)-3-acetylamino-4-one-6,7-dihydro-(3',4',6'-tri-O-acetyl-1',2'-dideoxy-β-D-glucopyranoso)[2',1'-f]-1,5-thiazepane
  参考文献：
  名称：

  Synthesis of fused bicyclic thioglycosides of N-acylated glucosamine as analogues of mycothiol

  摘要：

  The synthesis of a fused bicyclic thioglycoside analogue of mycothiol, (3R)-3-acetylamino-4-one-6,7-dihydro-(1',2'-dide-oxy-beta-D-glucopyranoso)[2',1'-f]-1,5-thiazepane (5), is reported. Treatment of phthalimido-protected peracetylated glucosamine with N-acetyl-cysteine and boron trifluoride-etherate gave the beta-linked thioglycoside, which was deprotected and cyclized, using HOBt and EDCl to form the lactam and giving the target structure. This mycothiol mimic and its tri-O-acetate will be investigated as potential inhibitors of enzymes involved in the biosynthesis of mycothiol. The protected derivative also has the potential to be an alpha-selective N-cysteinyl glucosamine donor, however, initial glycosylation attempts failed due to the apparent stability of the fused bicyclic system. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.04.019
• 作为产物：
  描述：

  (3R)-3-acetylamino-4-one-6,7-dihydro-(3',4',6'-tri-O-acetyl-1',2'-dideoxy-β-D-glucopyranoso)[2',1'-f]-1,5-thiazepane 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以82%的产率得到(3R)-3-acetylamino-4-one-6,7-dihydro-(1',2'-dideoxy-β-D-glucopyranoso)[2',1'-f]-1,5-thiazepane
  参考文献：
  名称：

  Synthesis of fused bicyclic thioglycosides of N-acylated glucosamine as analogues of mycothiol

  摘要：

  The synthesis of a fused bicyclic thioglycoside analogue of mycothiol, (3R)-3-acetylamino-4-one-6,7-dihydro-(1',2'-dide-oxy-beta-D-glucopyranoso)[2',1'-f]-1,5-thiazepane (5), is reported. Treatment of phthalimido-protected peracetylated glucosamine with N-acetyl-cysteine and boron trifluoride-etherate gave the beta-linked thioglycoside, which was deprotected and cyclized, using HOBt and EDCl to form the lactam and giving the target structure. This mycothiol mimic and its tri-O-acetate will be investigated as potential inhibitors of enzymes involved in the biosynthesis of mycothiol. The protected derivative also has the potential to be an alpha-selective N-cysteinyl glucosamine donor, however, initial glycosylation attempts failed due to the apparent stability of the fused bicyclic system. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.04.019