(5Xi)-2,3,4-三-O-苄基-6-脱氧-1-O-(4-硝基苯甲酰)-beta-D-来苏-吡喃己糖 | 151909-88-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (5Xi)-2,3,4-三-O-苄基-6-脱氧-1-O-(4-硝基苯甲酰)-beta-D-来苏-吡喃己糖
• 英文名称: 1-O-p-nitrobenzoyl 2,3,4-tri-O-benzyl-L-fucopyranose
• 英文别名: 2,3,4-Tri-O-benzyl-1-O-(4-nitrobenzoyl)-L-fucopyranose；[(3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl] 4-nitrobenzoate
• CAS: 151909-88-5
• 化学式: C₃₄H₃₃NO₈
• 分子量: 583.638
• InChiKey: FPWKKDQDBGGPFW-DPCMSISUSA-N

物化性质

• 熔点：
  136-139°C
• 溶解度：
  可溶于二氯甲烷、乙醚、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (5Xi)-2,3,4-三-O-苄基-6-脱氧-1-O-(4-硝基苯甲酰)-beta-D-来苏-吡喃己糖 在 sodium tetrahydroborate 、 二甲基硫 、 偶氮二异丁腈 、 四甲基乙二胺 、 三氟甲磺酸三甲基硅酯 、 氨 、 三正丁基氢锡 、 sodium acetate 、 臭氧 、 三乙胺 、 magnesium bromide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙腈 、 苯 为溶剂， 反应 12.68h， 生成 (2R,3R,4R,5R,6S)-3-Benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-5-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-4-ol
  参考文献：
  名称：

  Preferred conformation of C-glycosides. 10. Synthesis and conformational analysis of carbon trisaccharides

  摘要：

  A flexible and efficient synthesis of the carbon trisaccharide 2 related to the Type II O(H) blood group determinant has been developed. This route was applied to the synthesis of the trisaccharides 3, 4, and 5. The preferred solution conformations of compounds 2-5 were determined on the basis of vicinal coupling constants in the H-1 NMR spectrum. Each of the four trisaccharides adopts a distinct and well-defined solution conformation in accord with the predictions made on the basis of the preference of the C-glycosidic bond for the ''exo-anomeric'' conformation and the analysis of 1,3-diaxial-like interactions around the C-aglyconic bond.

  DOI：

  10.1021/jo00028a019
• 作为产物：
  描述：

  4-硝基苯甲酰氯 、 (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol 在 三乙胺 作用下， 以 乙醚 为溶剂， 生成 (5Xi)-2,3,4-三-O-苄基-6-脱氧-1-O-(4-硝基苯甲酰)-beta-D-来苏-吡喃己糖
  参考文献：
  名称：

  Preferred conformation of C-glycosides. 10. Synthesis and conformational analysis of carbon trisaccharides

  摘要：

  A flexible and efficient synthesis of the carbon trisaccharide 2 related to the Type II O(H) blood group determinant has been developed. This route was applied to the synthesis of the trisaccharides 3, 4, and 5. The preferred solution conformations of compounds 2-5 were determined on the basis of vicinal coupling constants in the H-1 NMR spectrum. Each of the four trisaccharides adopts a distinct and well-defined solution conformation in accord with the predictions made on the basis of the preference of the C-glycosidic bond for the ''exo-anomeric'' conformation and the analysis of 1,3-diaxial-like interactions around the C-aglyconic bond.

  DOI：

  10.1021/jo00028a019

文献信息

• Syntheses and Evaluation of Biantennary Oligosaccharide Ligands Mimicking Sialyl Lewis X.
  作者：Masahiro SAKAGAMI、Kazutoshi HORIE、Kunio HIGASHI、Harutami YAMADA、Hiroshi HAMANA

  DOI：10.1248/cpb.47.1237

  日期：——

  Sialyl Lewis X (1) is known to be a ligand of the cell adhesion molecule E-selectin. We have synthesized several biantennary glycoside-terminated ligands mimicking sialyl Lewis X (1), and evaluated their binding activity to E-selectin using HL-60 cells expressing sialyl Lewis X epitope and human umbilical vein endothelial cells (HUVECs). These compounds were found to possess moderate binding activities

  唾液酸路易斯X（1）是细胞粘附分子E-选择素的配体。我们已经合成了几种模拟唾液酸路易斯X（1）的双触角糖苷末端的配体，并使用表达唾液酸路易斯X表位和人脐静脉内皮细胞（HUVEC）的HL-60细胞评估了它们与E-选择素的结合活性。发现这些化合物具有对E-选择蛋白的中等结合活性。其中，没有唾液酸羧酸酯基的二岩藻糖苷类似物（8）比具有唾液酸-半乳糖残基和岩藻糖残基的2（IC50，8：4.7mM，2：11.7mM）具有更高的活性。此外，在角叉菜胶诱导的大鼠体内胸膜炎模型中，发现8可以减少炎症病变处的中性粒细胞浸润。
• A Novel Glycosidation Promoted by the Combination of Trimethylsilyl Halide and Zinc Triflate.
  作者：Kunio HIGASHI、Hiroshi SUSAKI

  DOI：10.1248/cpb.40.2019

  日期：——

  A novel glycosidation method has been developed which utilizes a trimethylsilyl halide-zinc triflate catalyst system to activate various benzyl-protected fucosyl, glucosyl and galactosyl esters. The promoter system was extended to use benzyl-protected alkyl glycosides and N-2, 2, 2, -trichloroethoxycarbonyl-protected glucosaminyl and galactosaminyl acetates as glycosyl donors.

  我们开发了一种新型糖苷化方法，它利用三甲基硅卤化物-三late锌催化剂体系来激活各种苄基保护的岩藻糖基、葡萄糖基和半乳糖基酯。该促进剂体系已扩展到使用苄基保护的烷基糖苷和 N-2，2，2，-三氯乙氧羰基保护的葡萄糖氨酰和半乳糖氨酰醋酸盐作为糖基供体。
• Preferred conformation of C-glycosides. 10. Synthesis and conformational analysis of carbon trisaccharides
  作者：Toru Haneda、Peter G. Goekjian、Sung H. Kim、Yoshito Kishi

  DOI：10.1021/jo00028a019

  日期：1992.1

  A flexible and efficient synthesis of the carbon trisaccharide 2 related to the Type II O(H) blood group determinant has been developed. This route was applied to the synthesis of the trisaccharides 3, 4, and 5. The preferred solution conformations of compounds 2-5 were determined on the basis of vicinal coupling constants in the H-1 NMR spectrum. Each of the four trisaccharides adopts a distinct and well-defined solution conformation in accord with the predictions made on the basis of the preference of the C-glycosidic bond for the ''exo-anomeric'' conformation and the analysis of 1,3-diaxial-like interactions around the C-aglyconic bond.