N-benzyloxycarbonyl-O-(3,4,6-tri-O-acetyl-2-N-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-threonine tert-butyl ester | 144923-64-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-benzyloxycarbonyl-O-(3,4,6-tri-O-acetyl-2-N-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-threonine tert-butyl ester
• 英文别名: tert-butyl (2S,3R)-3-[(2R,3R,4R,5S,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-(prop-2-enoxycarbonylamino)oxan-2-yl]oxy-2-(phenylmethoxycarbonylamino)butanoate
• CAS: 144923-64-8
• 化学式: C₃₂H₄₄N₂O₁₄
• 分子量: 680.706
• InChiKey: RDURSHAKAIHFIZ-ZXUYPCKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  48.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  200.32
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-O-(3,4,6-tri-O-acetyl-2-N-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-threonine tert-butyl ester 在 四(三苯基膦)钯 丙二酸二甲酯 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到(2S,3R)-2-Benzyloxycarbonylamino-3-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-amino-tetrahydro-pyran-2-yloxy)-butyric 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：

  N-苄氧羰基-L-苏氨酸 在 4 A molecular sieve 、 氰化汞 、 N,N'-二环己基碳二亚胺 、 copper(l) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 N-benzyloxycarbonyl-O-(3,4,6-tri-O-acetyl-2-N-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-threonine 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