ethyl 2-acetamido-6-S-(5-tert-butoxycarbonylamino-5-deoxy-β-D-arabinopyranosyl)-2-deoxy-1,6-dithio-β-D-glucopyranoside | 161418-93-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-acetamido-6-S-(5-tert-butoxycarbonylamino-5-deoxy-β-D-arabinopyranosyl)-2-deoxy-1,6-dithio-β-D-glucopyranoside
• CAS: 161418-93-5
• 化学式: C₂₀H₃₆N₂O₉S₂
• 分子量: 512.646
• InChiKey: NSFLVQZWTPCXDH-XJGKOXRFSA-N

物化性质

• 沸点：
  752.3±60.0 °C(predicted)
• 密度：
  1.42±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.92
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  169.02
• 氢给体数：
  6.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-acetamido-6-S-(5-tert-butoxycarbonylamino-5-deoxy-β-D-arabinopyranosyl)-2-deoxy-1,6-dithio-β-D-glucopyranoside 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 ethyl 2-acetamido-6-S-(5-amino-5-deoxy-β-D-arabinopyranosyl)-2-deoxy-1,6-dithio-β-D-glucopyranoside TFA salt
  参考文献：
  名称：

  Synthesis of azapyranosyl thioglycoside: Novel pseudo-disaccharide having an azasugar residue at the non-reducing end

  摘要：

  The first synthesis of azapyranosyl pseudo-disaccharide was described. Glycosidation of N-Boc-5-amino-5-deoxy-D-arabinose with N-acetyl-6-thio-D-glucosaminide in the presence of TsOH gave the corresponding 1,2-cis linked thioglycoside exclusively. The interglycosidic linkage was proved to be stable enough for the deprotection of N-Boc group by TFA.

  DOI：

  10.1016/s0040-4039(00)73128-5
• 作为产物：
  描述：

  5-azido-5-deoxy-D-arabinofuranose 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 sodium methylate 、 对甲苯磺酸 作用下， 以 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 38.0h， 生成 ethyl 2-acetamido-6-S-(5-tert-butoxycarbonylamino-5-deoxy-β-D-arabinopyranosyl)-2-deoxy-1,6-dithio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of ethyl 2-acetamido-6-S-(5-amino-5-deoxy-β-d-arabinopyranosyl)-2-deoxy-1,6-dithio-β-d-glucopyranoside: a sulfur-linked 5-amino-5-deoxyglycopyranosyl disaccharide

  摘要：

  A novel pseudo-disaccharide having an imino sugar residue at the non-reducing end, namely, a sulfur-linked 5-amino-5-deoxyglycopyranosyl disaccharide, which is a potential specific inhibitor for glycosidases that recognize not only the glycosidic linkage but also the aglycone moiety, was synthesized. Glycosidation of N-Boc-5-amino-5-deoxy-D-arabinose with ethyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-1,6-dithio-beta-D- glucopyranoside in the presence of TsOH gave exclusively the corresponding 1,2-cis-linked thioglycoside. The interglycosidic linkage proved stable enough under conditions for the deprotection of the N-Boc group with TFA. This pseudodisaccharide was unstable at pH > 5, but stable at lower pH. The sulfur-linked 5-amino-5-deoxyglycopyranosyl disaccharide was shown to be formed from 5-amino-5-deoxy-D-arabinose and ethyl 2-acetamido-2-deoxy-1,6-dithio-beta-D-glucopyranoside in an acidic buffer solution.

  DOI：

  10.1016/s0008-6215(99)00253-0