benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside | 51450-10-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: benzyl-3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-1-thio-β-D-glucopyranoside
• CAS: 51450-10-3
• 化学式: C₂₁H₂₇NO₈S
• 分子量: 453.513
• InChiKey: YHZMBYBQOMSIOQ-ONUIULTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  117.23
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside 在 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 以97%的产率得到benzyl 2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  2-乙酰氨基-2-脱氧-D-葡萄糖的S-，N-和O-糖基衍生物，以及潜在的化疗药物和疏水性糖苷配基和N-乙酰基-β-D-氨基葡萄糖苷酶抑制剂。

  摘要：

  已经获得了2-乙酰氨基-2-脱氧-D-葡萄糖与疏水性糖苷配基的S-，N-和O-糖基衍生物作为潜在的血浆膜活性剂。将2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-1-硫代-β-D-吡喃葡萄糖（6）转化为苄基，二苯甲基，三苯甲基和其他硫代糖苷。酰化6得到金刚烷基和卤代乙酰基衍生物。从相应的6的NH2-1和OH-1类似物获得了一系列类似的N-和O-糖基衍生物，例如O-和N-二硝基苯基，O-和N-金刚烷基以及N-4-甲基亚苄基衍生物。发现几种N-和S-糖基衍生物可在体外抑制小鼠的乳腺腺癌（TA3）细胞以及牛肉肝中的N-乙酰基-β-D-氨基葡萄糖苷酶。

  DOI：

  10.1016/0008-6215(84)85124-1
• 作为产物：
  描述：

  溴甲苯 、 β-D-葡萄糖胺五乙酸酯 在 三氟化硼乙醚 、 硫脲 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 4.08h， 以75%的产率得到benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Conjugates of plumbagin and phenyl-2-amino-1-thioglucoside inhibit MshB, a deacetylase involved in the biosynthesis of mycothiol

  摘要：

  N-Acetylglucosaminylinositol (GlcNAc-Ins)-deacetylase (MshB) and mycothiol-S-conjugate amidase (Mca), structurally related amidases present in mycobacteria and other Actinomycetes, are involved in the biosynthesis of mycothiol and in the detoxification of xenobiotics as their mycothiol-S-conjugates, respectively. With substrate analogs of GlcNAc-Ins, MshB showed a marked preference for inositol as the aglycon present in GlcNAc-Ins. The inhibition of MshB and Mca by 10 thioglycosides, 7 cyclohexyl-2-deoxy-2-C-alkylglucosides, and 4 redox cyclers was evaluated. The latter contained plumbagin tethered via 2 to 5 methylene carbons and an amide linkage to phenyl-2-deoxy-2-amino-1-thio-alpha-D-glucopyranoside. These proved to be the most potent amongst the 21 compounds tested as inhibitors of MshB. Their inhibitory potency varied with the length of the spacer, with the compound with longest spacer being the most effective. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.02.049

文献信息

• Microwave Irradiation for Accelerating the Synthesis of Thioglycosides
  作者：E. S. H. El Ashry、L. F. Awad、H. M. Abdel Hamid、A. I. Atta

  DOI：10.1080/00397910600767314

  日期：2006.9.1

  A simple and efficient procedure for the synthesis of thioglycosides has been achieved from the reaction of glycosylisothiouronium salts with alkyl or heteroaryl halides under microwave irradiation, in much shorter times and in yields comparable with conventional methods.