ethyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside | 99409-25-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• 英文别名: ethyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside；ethyl 6-O-benzyl-2-deoxy-2-phthalimido-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-thio-β-D-glucopyranoside
• CAS: 99409-25-3
• 化学式: C₅₀H₅₃NO₁₀S
• 分子量: 860.038
• InChiKey: GLAXRXCNUPIKFQ-FFHFIMDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.59
• 重原子数：
  62.0
• 可旋转键数：
  18.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  122.22
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  ethyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 2,4,6-三甲基吡啶 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.5h， 以53%的产率得到ethyl 6-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  包含α-L-富勒基糖基的四糖和九糖的合成，是糖蛋白碳水化合物部分复杂类型的一部分。

  摘要：

  三氟甲磺酸甲酯促进的6-O-苄基-2-脱氧-2-邻苯二甲酰亚胺基-4-O-（2,3,4,6-四-O-乙酰基-β-D-吡喃半乳糖基）-1-硫基缩合-3-O-（2,3,4-三-O-苄基-α-L-呋喃核糖基）-β-D-吡喃葡萄糖苷与苄基3,4,6-三-O-苄基-α-D-甘露吡喃糖苷和苄基2,4-二-O-苄基-3,6-二-O-（3,4,6-三-O-苄基-α-D-甘露吡喃糖基）-al ha-D-甘露吡喃糖苷得到四糖和九糖衍生物。除去保护基并进行N-乙酰化后，得到四糖1和九糖2。（公式：参见文字）。

  DOI：

  10.1016/0008-6215(85)90012-6
• 作为产物：
  描述：

  ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-thio-β-D-glucopyranoside 在 4 A molecular sieve 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以90%的产率得到ethyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a tetrasaccharide fragment of cobra venom factor oligosaccharide

  摘要：

  Synthesis of a tetrasaccharide fragment, alpha-L-Fuc-(1-->3)-beta-D-GlcNAc-(1-->2)-alpha-D-Man-(1-->6)-alpha-D-Man-OMe of the cobra venom factor (CVF) oligosaccharide is described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00107-x

文献信息

• Synthesis of a nonasaccharide with two lewis x trisaccharides anchored onto a branched trimannoside
  作者：Yong-Min Zhang、Annie Brodzky、Pierre Sinaÿ、Guillaume Saint-Marcoux、Bruno Perly

  DOI：10.1016/0957-4166(95)00146-g

  日期：1995.5

  Double condensation of phenyl 3,4,6-tri-O-benzyl-2-O-[6-O-benzyl-2-deoxy-2-phthalimido-4-O-(2 ,3,4,6-tetra-O-benzoyl-beta-D-galactopyranosyl)-3-O-(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-beta-D-glucopyranosyl]- 1-thio-alpha-D-mannopyranoside 31 with methyl 2,4-di-O-benzyl-beta-D-mannopyranoside 35, in the presence of N-iodosuccinimide/trifluoromethane-sulfonic acid, gave the protected nonasaccharide 36 in 60% yield. Conventional deprotection gave the nonasaccharide 1, in which two Lewis x trisaccharides are anchored onto a branched trimannoside.
• Synthesis of Fragments of the Glycocalyx Glycan of the ParasiteSchistosoma mansoni
  作者：Károly Ágoston、János Kerékgyártó、János Hajkó、Gyula Batta、Dirk J. Lefeber、Johannis P. Kamerling、Johannes F. G. Vliegenthart

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

  日期：2002.1.4

  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.