(S)-2-[(9H-Fluoren-9-ylmethoxycarbonyl)-methyl-amino]-3-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid pentafluorophenyl ester | 291311-50-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: (S)-2-[(9H-Fluoren-9-ylmethoxycarbonyl)-methyl-amino]-3-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid pentafluorophenyl ester
• 英文别名: (2,3,4,5,6-pentafluorophenyl) (2S)-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]-3-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxypropanoate
• CAS: 291311-50-7
• 化学式: C₃₉H₃₆F₅NO₁₄
• 分子量: 837.705
• InChiKey: VYQRLKNCUWDWDA-UFTDNPEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  59
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  180
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  (S)-2-[(9H-Fluoren-9-ylmethoxycarbonyl)-methyl-amino]-3-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid pentafluorophenyl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 N^α-acetyl-L-alanyl-(2-aminoprop-2-enoyl)-L-phenylalanine amide
  参考文献：
  名称：

  Deacetylation of Nα-methylated glycopeptides reveals that aza-enolates provide protection against β-elimination of carbohydrates O-linked to serine

  摘要：

  Three glycopeptides Ac-Ala-Ser[beta-Gal(OAc)(4)]-Phe-NH2, Ac-Ala-N-alpha-Me-Ser[beta-Gal(OAc)(4)]-Phe-NH2 and Ac-Ala-Ser[beta-Gal(OAc)(4)]-N-alpha-Me-Phe-NH2 have been prepared and treated with base in order to remove the O-acetyl protective groups. The glycopeptide which carried the N-methyl group on the glycosylated serine, was substantially more susceptible to beta-elimination than the two others. This reveals that formation of an aza-enolate from the amide bond to a glycosylated serine provides protection against p-elimination under basic conditions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00611-0
• 作为产物：
  描述：

  Fmoc-N-methyl-L-serine 在 三氟化硼乙醚 、 达卡巴嗪 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 (S)-2-[(9H-Fluoren-9-ylmethoxycarbonyl)-methyl-amino]-3-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid pentafluorophenyl ester
  参考文献：
  名称：

  Deacetylation of Nα-methylated glycopeptides reveals that aza-enolates provide protection against β-elimination of carbohydrates O-linked to serine

  摘要：

  Three glycopeptides Ac-Ala-Ser[beta-Gal(OAc)(4)]-Phe-NH2, Ac-Ala-N-alpha-Me-Ser[beta-Gal(OAc)(4)]-Phe-NH2 and Ac-Ala-Ser[beta-Gal(OAc)(4)]-N-alpha-Me-Phe-NH2 have been prepared and treated with base in order to remove the O-acetyl protective groups. The glycopeptide which carried the N-methyl group on the glycosylated serine, was substantially more susceptible to beta-elimination than the two others. This reveals that formation of an aza-enolate from the amide bond to a glycosylated serine provides protection against p-elimination under basic conditions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00611-0