N-[(1R)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-galactitolspiro[1.4]-2-benzyloxycarbonylaminomethyl-2-oxazolin-5-ylidene]glycine methylester | 1337568-68-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[(1R)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-galactitolspiro[1.4]-2-benzyloxycarbonylaminomethyl-2-oxazolin-5-ylidene]glycine methylester
• 英文别名: methyl 2-[[(5R,7R,8S,9S,10R)-8,9,10-triacetyloxy-7-(acetyloxymethyl)-2-(phenylmethoxycarbonylaminomethyl)-3,6-dioxa-1-azaspiro[4.5]dec-1-en-4-ylidene]amino]acetate
• CAS: 1337568-68-9
• 化学式: C₂₈H₃₃N₃O₁₄
• 分子量: 635.582
• InChiKey: ADGKUEPYARRHIN-HSESPGHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  45
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  213
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  N-[(1R)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-galactitolspiro[1.4]-2-benzyloxycarbonylaminomethyl-2-oxazolin-5-ylidene]glycine methylester 以 二氯甲烷 、 水 为溶剂， 以27%的产率得到N-(2,3,4,6-tetra-O-acetyl-1-deoxy-1-Z-glycylamido-β-D-galactopyranosylcarbonyl)glycine methylester
  参考文献：
  名称：

  Ritter-type reaction of C-(1-bromo-1-deoxy-d-glycopyranosyl)formamides and its application for the synthesis of oligopeptides incorporating anomeric α-amino acids

  摘要：

  O-Peracetylated or -perbenzoylated C-(1-bromo-1-deoxy-D-glycopyranosyl)formamides of D-gluco, D-galacto, and D-arabino configuration were reacted with Ag(I)-salts or HgO in nitrile solvents to give N-acyl-1-cyano-D-glycopyranosylamines with an axial C-N bond at the anomeric centre. In the presence of HgBr2, Hg(CN)(2), or InCl3 the anomer of the above glycosylamine with an equatorial C-N bond was also isolated or detected. In CH3NO2 solutions as few as 5-10 equiv of the nitrile were sufficient to get acceptable yields for the products. Under similar conditions N-substituted C-(2,3,4,6-tetra-O-acetyl-1-bromo-1-deoxy-beta-D-galactopyranosyl)formamides gave anomeric spiro-oxazoline derivatives which, upon mild acidic hydrolysis, opened up to di- and tripeptides of anomeric alpha-amino acids. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.07.001
• 作为产物：
  描述：

  N-(3,4,5,7-tetra-O-acetyl-2-bromo-2-deoxy-α-D-galacto-hept-2-ulopyranosonoyl)glycine methyl ester 、 N-苄氧羰基氨基乙腈 在 silver carbonate 作用下， 以 硝基甲烷 为溶剂， 反应 144.0h， 以29%的产率得到N-[(1R)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-galactitolspiro[1.4]-2-benzyloxycarbonylaminomethyl-2-oxazolin-5-ylidene]glycine methylester
  参考文献：
  名称：

  Ritter-type reaction of C-(1-bromo-1-deoxy-d-glycopyranosyl)formamides and its application for the synthesis of oligopeptides incorporating anomeric α-amino acids

  摘要：

  O-Peracetylated or -perbenzoylated C-(1-bromo-1-deoxy-D-glycopyranosyl)formamides of D-gluco, D-galacto, and D-arabino configuration were reacted with Ag(I)-salts or HgO in nitrile solvents to give N-acyl-1-cyano-D-glycopyranosylamines with an axial C-N bond at the anomeric centre. In the presence of HgBr2, Hg(CN)(2), or InCl3 the anomer of the above glycosylamine with an equatorial C-N bond was also isolated or detected. In CH3NO2 solutions as few as 5-10 equiv of the nitrile were sufficient to get acceptable yields for the products. Under similar conditions N-substituted C-(2,3,4,6-tetra-O-acetyl-1-bromo-1-deoxy-beta-D-galactopyranosyl)formamides gave anomeric spiro-oxazoline derivatives which, upon mild acidic hydrolysis, opened up to di- and tripeptides of anomeric alpha-amino acids. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.07.001