ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside | 183051-70-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2-ethoxy-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-4-ol
• CAS: 183051-70-9
• 化学式: C₂₉H₃₄O₆
• 分子量: 478.585
• InChiKey: FBJRKUPDVLAIBD-JYJZCUDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside 在 甲醇 、 calcium sulfate 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 左旋樟脑磺酸 、 sodium methylate 、 silver perchlorate 、 一水合肼 、 silver carbonate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 83.17h， 生成
  参考文献：
  名称：

  A highly practical synthesis of the sialyl Lewis X pentasaccharide and an investigation of binding to E-, P-, and L-Selectins

  摘要：

  A practical synthesis of the sialyl Lewis X (sLe(x)) pentasaccharide, NeuAc alpha 2-3Gal beta 1-4(Fuc alpha 1-3)GlcNAc alpha 1-3Gal beta OEt (1), as a potential blocker for E-selectin has been described. The glycosylation of a trisaccharide acceptor, Fuc alpha(1-3)GlcNAc beta(1-3)Gal beta OEt, with a disaccharide donor, NeuAc alpha(2-3)Gal beta SMe, did not yield the desired sLe(x) pentasaccharide 1 at all. However, the glycosylation of a disaccharide acceptor, GlcNAc beta(1-3)Gal beta OEt, with a disaccharide donor, NeuAc alpha(2-3)Gal beta SMe, quantitatively yielded the tetrasaccharide NeuAc alpha(2-3)Gal beta(1-4)GlcNAc beta(1-3)Gal beta OEt. This tetrasaccharide is readily converted to the title compound in a high yield by fucosylation, followed by deprotection. The inhibitory activities of compound 1 toward the binding of the natural ligand (sLe(x)) with the E-, P-, and L-selectins were stronger than those of the sLe(x) tetrasaccharide. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00105-8
• 作为产物：
  描述：

  ethyl 2,4,6-tri-O-benzyl-3-O-(4-methoxybenzyl)-β-D-galactopyranoside 在 ammonium cerium(IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以94%的产率得到ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  A highly practical synthesis of the sialyl Lewis X pentasaccharide and an investigation of binding to E-, P-, and L-Selectins

  摘要：

  A practical synthesis of the sialyl Lewis X (sLe(x)) pentasaccharide, NeuAc alpha 2-3Gal beta 1-4(Fuc alpha 1-3)GlcNAc alpha 1-3Gal beta OEt (1), as a potential blocker for E-selectin has been described. The glycosylation of a trisaccharide acceptor, Fuc alpha(1-3)GlcNAc beta(1-3)Gal beta OEt, with a disaccharide donor, NeuAc alpha(2-3)Gal beta SMe, did not yield the desired sLe(x) pentasaccharide 1 at all. However, the glycosylation of a disaccharide acceptor, GlcNAc beta(1-3)Gal beta OEt, with a disaccharide donor, NeuAc alpha(2-3)Gal beta SMe, quantitatively yielded the tetrasaccharide NeuAc alpha(2-3)Gal beta(1-4)GlcNAc beta(1-3)Gal beta OEt. This tetrasaccharide is readily converted to the title compound in a high yield by fucosylation, followed by deprotection. The inhibitory activities of compound 1 toward the binding of the natural ligand (sLe(x)) with the E-, P-, and L-selectins were stronger than those of the sLe(x) tetrasaccharide. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00105-8

文献信息

• One-Pot Synthesis of Lewis X Oligosaccharide Derivatives Using "Armed-Disarmed" Coupling Method
  作者：Masahiro Yoshida、Takao Kiyoi、Takahiro Tsukida、Hirosato Kondo

  DOI：10.1080/07328309808002344

  日期：1998.5.1

  Abstract A stereocontrolled synthesis of Lex oligosaccharide derivatives using a facile one-pot, two-step glycosylation based on the “Armed-Disarmed” concept are described. The first coupling of phenyl O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galacto-pyranosyl)-(1→4)-2,6-di-O-benzoyl-1-thio-β-D-glucopyranoside (2) with phenyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (3) using N-iodosuccinimide (N

  摘要描述了一种基于“武装解除”概念的简便的一锅两步糖基化立体控制合成Lex寡糖衍生物的方法。苯基O-（2,6-二-O-苯甲酰基-3,4-O-异亚丙基-β-D-半乳糖-吡喃糖基）-（1→4）-2,6-二-O-苯甲酰基的首次偶联使用N-碘代琥珀酰亚胺（NIS）-三氟甲磺酸（-1）将-1-硫代-β-D-吡喃葡萄糖苷（2）与苯基2,3,4-三-O-苄基-1-硫代-β-L-呋喃果糖苷（3）（ （TfOH）得到三糖（8），将其未经纯化而进行第二次缩合，用一些受体如2,4,6-三-O-苄基-β-D-D-吡喃半乳糖苷（4），2,6-二乙基乙基-O-苯甲酰基-β-D-吡喃半乳糖苷（5），乙基O-（2,6-二-O-苄基-β-D-吡喃半乳糖基）-（1→4）-2,3,6-tri-O -苄基-β-D-吡喃葡萄糖苷（6）和乙基O-（2,6-二-O-苯甲酰基-β-D-吡喃半乳糖基）-（1→4）-2,3，6-三-O-苄基