N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-L-serine pentafluorophenyl ester | 291311-49-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-L-serine pentafluorophenyl ester
• 英文别名: L-Serine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-, pentafluorophenyl ester；(2,3,4,5,6-pentafluorophenyl) (2S)-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]-3-hydroxypropanoate
• CAS: 291311-49-4
• 化学式: C₂₅H₁₈F₅NO₅
• 分子量: 507.414
• InChiKey: IYRBQKAPTCBDNG-KRWDZBQOSA-N

物化性质

• 沸点：
  610.7±55.0 °C(Predicted)
• 密度：
  1.461±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-L-serine pentafluorophenyl ester 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 Ac-Ala-N^α-Me-Ser[β-Gal(OAc)4]-Phe-NH2
  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：

  9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 达卡巴嗪 、 三乙胺 作用下， 以 水 、 乙酸乙酯 、 乙腈 为溶剂， 生成 N^α-(fluoren-9-ylmethoxycarbonyl)-N^α-methyl-L-serine 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

文献信息

• Use of Fluorobenzoyl Protective Groups in Synthesis of Glycopeptides:  β-Elimination of <i>O</i>-Linked Carbohydrates Is Suppressed
  作者：Petter Sjölin、Jan Kihlberg

  DOI：10.1021/jo001584q

  日期：2001.5.1

  Fluorobenzoyl groups have been investigated as alternatives to acetyl and benzoyl protective groups in carbohydrate and glycopeptide synthesis. D-Glucose and lactose were protected with different fluorobenzoyl groups and then converted into glycosyl bromides in high yields (> 80% over two steps). Glycosylation of protected derivatives of serine with these donors gave 1,2-trans glycosides in good yields (similar to 60-70%) and excellent stereoselectivity without formation of ortho esters. The resulting glycosylated amino acid building blocks were then used in solid-phase synthesis of two model O-linked glycopeptides known to be unusually sensitive to beta -elimination on base-catalyzed deacylation. When either a 3-fluoro- or a 2,5-difluorobenzoyl group was used for protection of each of the two model glycopeptides the extent of beta -elimination decreased from 80% to 10% and from 50% to 0%, respectively, as compared to when using the ordinary benzoyl group. Fluorobenzoyl groups thus combine the advantages of the benzoyl group in formation of glycosidic bonds (i.e., high stereoselectivity and low levels of ortho ester formation) with the ease of removal characteristic of the acetyl group.
• Deacetylation of Nα-methylated glycopeptides reveals that aza-enolates provide protection against β-elimination of carbohydrates O-linked to serine
  作者：Petter Sjölin、Jan Kihlberg

  DOI：10.1016/s0040-4039(00)00611-0

  日期：2000.6

  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.