(3-trifluoroacetamidopropyl)-2-acetamido-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranoside | 303111-28-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3-trifluoroacetamidopropyl)-2-acetamido-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6S)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-[3-[(2,2,2-trifluoroacetyl)amino]propoxy]oxan-4-yl]oxy-3,4,5-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 303111-28-6
• 化学式: C₂₇H₃₉F₃N₂O₁₆
• 分子量: 704.606
• InChiKey: LMDCKGFPCBTUJI-NVKMBFJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  48
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  241
• 氢给体数：
  4
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  (3-trifluoroacetamidopropyl)-2-acetamido-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranoside 在 甲醇 、 sodium hydroxide 、 水 、 sodium methylate 、 silver trifluoromethanesulfonate 、 溶剂黄146 、 1,1,3,3-四甲基脲 、 锌 作用下， 生成
  参考文献：
  名称：

  Synthesis of N-acetyllactosamine-terminated oligosaccharides — fragments of glycoprotein O-chains

  摘要：

  The pentasaccharide Galbeta1-4GlcNAcbeta1-6(Galbeta1-4GlcNAcbeta1-3)GalNAcalphaOR, its partial trisaccharides Galbeta1-4GlcNAcbeta1-3GalNAcalphaOR and Galbeta1-4GlcNAcbeta1-6GalNAcalphaOR and the tetrasaccharide Galbeta1-4GlcNAcbeta1-6(Galbeta1-3)GalNAcalphaOR were synthesised as spacered derivatives (R = CH2CH2CH2NH2) using a Troc-protected lactosamine glycosyl donor at the key stage.

  DOI：

  10.1070/mc2002v012n05abeh001653
• 作为产物：
  描述：

  Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{(4aR,6S,7R,8R,8aR)-7-acetylamino-2-phenyl-6-[3-(2,2,2-trifluoro-acetylamino)-propoxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-tetrahydro-pyran-3-yl ester 在 溶剂黄146 作用下， 反应 3.0h， 以75%的产率得到(3-trifluoroacetamidopropyl)-2-acetamido-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranoside
  参考文献：
  名称：

  Simeoni; Byramova; Bovin, Russian Journal of Bioorganic Chemistry, 1999, vol. 25, # 1, p. 55 - 61

  摘要：

  DOI：

文献信息

• Simple stereoselective synthesis of α2-6 sialooligosaccharides
  作者：Galina Pazynina、Alexander Tuzikov、Alexander Chinarev、Polina Obukhova、Nicolai Bovin

  DOI：10.1016/s0040-4039(02)01983-4

  日期：2002.11

  The sialylation approach reported by A. Khorlin et. al 30 years ago has been modified into a highly practical procedure for stereoselective alpha2-6 sialylation of galactopyranose 4,6-diols. (C) 2002 Elsevier Science Ltd. All rights reserved.