ethyl 4-O-acetyl-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside | 419549-65-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4-O-acetyl-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside
• CAS: 419549-65-8
• 化学式: C₂₈H₃₁NO₇S
• 分子量: 525.623
• InChiKey: NEVBHVIGHNDKQO-MOBZEUQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  91.37
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-O-acetyl-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 以73%的产率得到ethyl 3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Fragments of the Glycocalyx Glycan of the ParasiteSchistosoma mansoni

  摘要：

  The chemical synthesis of alpha-L-Fucp-(1 --> 3)-beta-D-GalpNAc-(1 --> 4)-beta-D-GlcpNAc-(1 --> 3)-alpha-D-GalpO(CH2)(5)NH2, beta-D-GalpNAc-(1 --> 4)-[alpha-L-Fucp-(1 --> 3)-]beta-D-GlcpNAc-(1 --> 3)-alpha-D-GalpO(CH2)(5)NH2, and alpha-L-Fucp-(1 --> 3)-beta-D-GalpNAc-(1 --> 4)- [alpha-L-Fucp-(1 --> 3)-]beta-D-GlcpNAc-(1 --> 3)-alpha-D-GalpO(CH2)(5)NH2 is described. These structures represent fucosylated oligosaccharide fragments of the glycocalyx glycan of the cercarial stage of the parasite Schistosoma mansoni, and in protein-conjugated form they are potential diagnostics in the search for antibodies raised against the glycan in the serum of infected humans.

  DOI：

  10.1002/1521-3765(20020104)8:1<151::aid-chem151>3.0.co;2-c
• 作为产物：
  描述：

  ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 吡啶 、 三氯化铝 、 硼烷-三甲胺络合物 、 4 A molecular sieve 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 ethyl 4-O-acetyl-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Fragments of the Glycocalyx Glycan of the ParasiteSchistosoma mansoni

  摘要：

  The chemical synthesis of alpha-L-Fucp-(1 --> 3)-beta-D-GalpNAc-(1 --> 4)-beta-D-GlcpNAc-(1 --> 3)-alpha-D-GalpO(CH2)(5)NH2, beta-D-GalpNAc-(1 --> 4)-[alpha-L-Fucp-(1 --> 3)-]beta-D-GlcpNAc-(1 --> 3)-alpha-D-GalpO(CH2)(5)NH2, and alpha-L-Fucp-(1 --> 3)-beta-D-GalpNAc-(1 --> 4)- [alpha-L-Fucp-(1 --> 3)-]beta-D-GlcpNAc-(1 --> 3)-alpha-D-GalpO(CH2)(5)NH2 is described. These structures represent fucosylated oligosaccharide fragments of the glycocalyx glycan of the cercarial stage of the parasite Schistosoma mansoni, and in protein-conjugated form they are potential diagnostics in the search for antibodies raised against the glycan in the serum of infected humans.

  DOI：

  10.1002/1521-3765(20020104)8:1<151::aid-chem151>3.0.co;2-c

文献信息

• Synthesis of 2-Amino-2-deoxy-β-D-galactopyranosyl-(1→4)-2-amino-2-deoxy-β-D-galactopyranosides: Using Various 2-Deoxy-2-phthalimido-D-galactopyranosyl Donors and Acceptors
  作者：Jan Veselý、Miroslav Ledvina、Jindřich Jindřich、Tomáš Trnka、David Šaman

  DOI：10.1135/cccc20041914

  日期：——

  A systematic study is presented of the efficiency of the most common glycosylation methods using standard 2-deoxy-2-phthalimidogalactopyranosyl donors ethyl 4-O-acetyl-3,6-di-O- benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside (3a), 4-O-Acetyl-3,6-di-O-benzyl- 2-deoxy-2-phthalimido-β-D-galactopyranosyl bromide (4), 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl fluoride (5b), O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl) trichloroacetimidate (7) and ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside (8), pent-4-enyl 3,6-di-O-benzyl- and 3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside (10a) and (10b) and pent-4-enyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-4-O-(trimethylsilyl)-β-D-galactopyranoside (11) as glycosyl acceptors in the synthesis of 2-amino-2-deoxy-β-D-galactopyranosyl-(1→4)-2-amino-2-deoxy-β-D-galactopyranosides 12, 16a and 17a. It was found that due to a low reactivity of the axial OH(4) group of glycosyl acceptors, disaccharides 16b and 17b with α(1→4) bond were also formed. The unexpected intermolecular migration of ethylsufanyl group from the reducing end of glycosyl acceptor 8 the reducing end of the activated form of glycosyl donor 4 in the glycosylation step to give ethylsulfanyl derivative 3a was proved. For preparation of the glycosyl donors and glycosyl acceptors with galacto configuration an approach based on epimerization of 4-O-mesyl derivatives of appropriate synthons with gluco configuration 2a and 2b was employed.

  本文对使用标准2-去氧-2-邻苯二甲酰胺基半乳糖供体乙基4-O-乙酰基-3,6-双-O-苄基-2-去氧-2-邻苯二甲酰胺基-1-硫代-β-D-半乳糖苷（3a）、4-O-乙酰基-3,6-双-O-苄基-2-去氧-2-邻苯二甲酰胺基-β-D-半乳糖苷溴化物（4）、4-O-乙酰基-3,6-双-O-苄基-2-去氧-2-邻苯二甲酰胺基-β-D-半乳糖苷氟化物（5b）、O-(4-O-乙酰基-3,6-双-O-苄基-2-去氧-2-邻苯二甲酰胺基-β-D-半乳糖苷)三氯乙酰胺盐（7）和乙基3,6-双-O-苄基-2-去氧-2-邻苯二甲酰胺基-1-硫代-β-D-半乳糖苷（8）、戊-4-烯基3,6-双-O-苄基和3-O-烯基-6-O-苄基-2-去氧-2-邻苯二甲酰胺基-β-D-半乳糖苷（10a）和（10b）以及戊-4-烯基3,6-双-O-苄基-2-去氧-2-邻苯二甲酰胺基-4-O-(三甲基硅基)-β-D-半乳糖苷（11）作为糖基受体，在合成2-氨基-2-去氧-β-D-半乳糖苷-(1→4)-2-氨基-2-去氧-β-D-半乳糖苷12、16a和17a的过程中，对最常见的糖基化方法的效率进行了系统研究。由于糖基受体轴向OH(4)基团的低反应性，也形成了具有α(1→4)键的二糖16b和17b。证实了在糖基化步骤中，乙基硫基团从糖基受体8的还原端出现意外的分子间迁移，到糖基供体4的活化形式的还原端，形成乙基硫基衍生物3a。为了制备具有半乳糖构型的糖基供体和糖基受体，采用了基于4-O-甲磺基衍生物与具有葡萄糖构型的适当合成子的对映异构化的方法2a和2b。