N^α-(Fluoren-9-ylmethoxycarbonyl)-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-L-serine pentafluorophenyl ester | 149704-74-5

• 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^α-(Fluoren-9-ylmethoxycarbonyl)-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-L-serine pentafluorophenyl ester
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-oxo-3-(2,3,4,5,6-pentafluorophenoxy)propoxy]oxan-2-yl]methyl benzoate
• CAS: 149704-74-5
• 化学式: C₅₈H₄₂F₅NO₁₄
• 分子量: 1071.96
• InChiKey: IRTPEZYIYBYFKJ-KGLQZIJYSA-N

物化性质

• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  78
• 可旋转键数：
  23
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  188
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  N^α-(Fluoren-9-ylmethoxycarbonyl)-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-L-serine pentafluorophenyl ester 在 吗啉 、 甲醇 、 sodium methylate 、 碳酸氢钠 、 1-羟基苯并三唑 、 N,N-二甲基甲酰胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 N^α-(fluoren-9-ylmethoxycarbonyl)-O-(β-D-glucopyranosyl)-L-serine
  参考文献：
  名称：

  Reimer, Kerry B.; Meldal, Morten; Kusumoto, Shoichi, Journal of the Chemical Society. Perkin transactions I, 1993, # 8, p. 925 - 932

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2,3,4,6-戊-O-苯甲酰基-D-吡喃葡萄糖苷 在 3 A molecular sieve 、 氢溴酸 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 乙酸酐 、 溶剂黄146 为溶剂， 反应 4.5h， 生成 N^α-(Fluoren-9-ylmethoxycarbonyl)-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-L-serine pentafluorophenyl ester
  参考文献：
  名称：

  Use of Fluorobenzoyl Protective Groups in Synthesis of Glycopeptides:  β-Elimination of O-Linked Carbohydrates Is Suppressed

  摘要：

  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.

  DOI：

  10.1021/jo001584q

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.
• Reimer, Kerry B.; Meldal, Morten; Kusumoto, Shoichi, Journal of the Chemical Society. Perkin transactions I, 1993, # 8, p. 925 - 932
  作者：Reimer, Kerry B.、Meldal, Morten、Kusumoto, Shoichi、Fukase, Koichi、Bock, Klaus

  DOI：——

  日期：——