3-trifluoroacetamidopropyl 2-acetamido-6-O-benzyl-2-deoxy-β-D-glucopyranoside | 121042-73-7

• 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-6-O-benzyl-2-deoxy-β-D-glucopyranoside
• 英文别名: N-[3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(phenylmethoxymethyl)oxan-2-yl]oxypropyl]-2,2,2-trifluoroacetamide
• CAS: 121042-73-7
• 化学式: C₂₀H₂₇F₃N₂O₇
• 分子量: 464.439
• InChiKey: QJEKAHFWZNFLFJ-DUQPFJRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-trifluoroacetamidopropyl 2-acetamido-6-O-benzyl-2-deoxy-β-D-glucopyranoside 在 sodium methylate 、 mercury(II) cyanide 、 mercury dibromide 作用下， 以 甲醇 、 硝基甲烷 、 甲苯 为溶剂， 反应 17.5h， 生成
  参考文献：
  名称：

  Synthesis of trisaccharide 6’ SiaLec and its 6-O-Su derivative

  摘要：

  The synthetic approach to 6'SiaLe(c) and its 6-O-Su derivative comprised alpha-sialylation of a protected Le(c) derivative, 2,3-di-OAcGal beta 1-3(3-OAc-6-OBn)GlcNAc beta 1-Osp (68% yield) as the key stage. Deprotection of the obtained trisaccharide (three stages, 79% overall yield) led to Neu5Ac alpha 2-6Gal beta 1-3GlcNAc beta 1-Osp; partial deprotection followed by selective sulfation and total deprotection - to Neu5Ac alpha 2-6Gal beta 1-3(6-O-Su)GlcNAc beta 1-Osp (four stages, 72% overall yield).

  DOI：

  10.1016/j.mencom.2012.06.007
• 作为产物：
  描述：

  β-Ac3GlcNAc-sp3 在 吡啶 、 盐酸 、 sodium methylate 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 54.0h， 生成 3-trifluoroacetamidopropyl 2-acetamido-6-O-benzyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Artificial antigens and affinity sorbents with groups specificities Lea, Leb, and Led

  摘要：

  DOI：

  10.1007/bf00598177

文献信息

• Synthesis of complex α2-3 sialooligosaccharides, including sulfated and fucosylated ones, using Neu5Acα2-3Gal as a building block
  作者：Galina V. Pazynina、Marina A. Sablina、Alexander B. Tuzikov、Alexander A. Chinarev、Nicolai V. Bovin

  DOI：10.1070/mc2003v013n06abeh001845

  日期：2003.1

  3-Aminopropyl glycosides of Neu5Acalpha2-3Galbeta, Neu5Acalpha2-3Galbeta1-4GlcNAcbeta, Neu5Acalpha2-3Galbeta1-4(6-HSO3)GlcNAcbeta, Neu5Acalpha2-3Galbeta1-3GalNAcalpha, Neu5Acalpha2-3Galbeta1-3(6-HSO3)GalNAcalpha, Neu5Acalpha2-3Galbeta1-3GlcNAcbeta, Neu5Acalpha2-3Galbeta1-3(6-HSO3)GlcNAcbeta, Neu5Acalpha2-3Galbeta1-3(Fucalpha1-4)GlcNAcbeta and Neu5Acalpha2-3Galbeta1-4(Fucalpha1-3)GlcNAcbeta were synthesised using protected Neu5Acalpha2-3Gal bromide as a glycosyl donor at the key stage.
• Function-spacer-lipid constructs of Lewis and chimeric Lewis/ABH glycans. Synthesis and use in serological studies
  作者：Ivan M. Ryzhov、Elena Yu. Korchagina、Alexander B. Tuzikov、Inna S. Popova、Tatiana V. Tyrtysh、Galina V. Pazynina、Stephen M. Henry、Nicolai V. Bovin

  DOI：10.1016/j.carres.2016.09.016

  日期：2016.11

  Seven lipophilic constructs containing Lewis (Le(a), Le(b), Le(y)) or chimeric Lewis/ABH (ALe(b), BLe(b), ALe(y), BLe(y)) glycans were obtained starting from corresponding oligosaccharides in form of 3-aminopropyl glycosides. ALe(b) and BLe(b) pentasaccharides were synthesized via [3 + 1] blockwise approach. The constructs (neoglycolipids, or FSLs) were inserted in erythrocyte membrane, and obtained "kodecytes" were used to map the immunochemical specificity of historical and contemporary monoclonal and polyclonal blood group system Lewis reagents. (C) 2016 Published by Elsevier Ltd.