N-benzyloxycarbonyl-O-<3,4,6-tri-O-acetyl-2-N-(2,2,2-trichloroethyloxycarbonyl)-amino-2-deoxy-β-D-glucopyranosyl>-serine tert-butyl ester | 144944-17-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-benzyloxycarbonyl-O-<3,4,6-tri-O-acetyl-2-N-(2,2,2-trichloroethyloxycarbonyl)-amino-2-deoxy-β-D-glucopyranosyl>-serine tert-butyl ester
• 英文别名: tert-butyl (2S)-3-[(2R,3R,4R,5S,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]oxy-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 144944-17-2
• 化学式: C₃₀H₃₉Cl₃N₂O₁₄
• 分子量: 758.004
• InChiKey: CXVOOKGCIKUQOZ-RLKHCHHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  49
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  200
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-O-<3,4,6-tri-O-acetyl-2-N-(2,2,2-trichloroethyloxycarbonyl)-amino-2-deoxy-β-D-glucopyranosyl>-serine tert-butyl ester 在 溶剂黄146 、 锌 作用下， 以90%的产率得到(S)-2-Benzyloxycarbonylamino-3-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-amino-tetrahydro-pyran-2-yloxy)-propionic acid tert-butyl ester
  参考文献：
  名称：

  Enzymatic glycosylation of o-glycopeptides

  摘要：

  O-Glycosylation of serine derivatives carried out with N-urethane protected glucosamine yields O-glycopeptides which are regio-and stereoselectively galactosylated with the aid of beta-1,4-galactosyltransferase (EC2.4.1.22).

  DOI：

  10.1016/s0040-4039(00)79082-4
• 作为产物：
  描述：

  2-deoxy-2-amino glucose 在 吡啶 、 盐酸 、 4 A molecular sieve 、 三氟化硼乙醚 、 DMTST 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 3.5h， 生成 N-benzyloxycarbonyl-O-<3,4,6-tri-O-acetyl-2-N-(2,2,2-trichloroethyloxycarbonyl)-amino-2-deoxy-β-D-glucopyranosyl>-serine tert-butyl ester
  参考文献：
  名称：

  Synthetic O-glycopeptides as model substrates for glycosyltransferases

  摘要：

  A new approach to O-glycopeptides of the glucosamine type is described. N-Urethane protected, peracetylated glucosamine is converted into its 1-thio (1-bromo) derivative and used for glycosylation of a variety of protected serine or threonine derivatives as acceptors. The urethane group is easily exchanged for the natural N-acetyl moiety and O-deacetylation is achieved with hydrazine/methanol. The resulting O-GlcNAc derivatives are subjected to an enzymatic galactosylation procedure using beta-1,4-galactosyluwsferase (EC 2.4.1.22) to furnish O-glycopeptides of the neolactosamine type.

  DOI：

  10.1016/s0957-4166(00)80230-x