phenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside | 153889-76-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• 英文别名: phenyl-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside；[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3S,4R,5R,6S)-4-acetyloxy-2-(acetyloxymethyl)-5-(1,3-dioxoisoindol-2-yl)-6-phenylsulfanyloxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 153889-76-0
• 化学式: C₃₈H₄₁NO₁₇S
• 分子量: 815.806
• InChiKey: BAMPLOFPSSUXHZ-HTHPTONZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  57
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  248
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  phenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-nitrophenyl O-β-D-galactopyranosyl-(1->4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->6)-2-acetamido-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  A convenient synthesis of N-acetyllactosamine-linked oligosaccharides from phenyl 3,6,2′,3′,4′,6′-hexa-O-acetyl- 2-deoxy-2-phthalimido-1-thio-β-lactopyranoside

  摘要：

  DOI：

  10.1016/0008-6215(93)87042-q
• 作为产物：
  描述：

  苯基硫三甲基硅烷 、 2-邻苯二甲酰亚胺基乳糖胺,七乙酸酯 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以77%的产率得到phenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  A convenient synthesis of N-acetyllactosamine-linked oligosaccharides from phenyl 3,6,2′,3′,4′,6′-hexa-O-acetyl- 2-deoxy-2-phthalimido-1-thio-β-lactopyranoside

  摘要：

  DOI：

  10.1016/0008-6215(93)87042-q

文献信息

• Synthesis of Fluorine-Containing Core-2 Tetrasaccharides
  作者：Khushi Matta、Jie Xia、James Alderfer、Conrad Piskorz、Robert Locke

  DOI：10.1055/s-2003-40342

  日期：——

  Synthesis of core-2 branched tetrasaccharides 1-3, in which a fluorine atom was substituted at the 3 or 4-position of galactose residues is described. Glycosyl imidates 13, and 19 were prepared and used to provide novel glycosyl disaccharide donors 15 and 21, respectively. Coupling of acceptor 7 with glycosyl bromide 6 provides a disaccharide that was further converted into disaccharide acceptor 8. The coupling of acceptor 14 with donor 13, and acceptor 20 with donor 19 provided disaccharides that were converted to disaccharide donors 15 and 21, respectively. Regioselective glycosylation of acceptors 8, and 16 with donors 9, 15, and 21 provided tetrasaccharides 10, 17, and 22 respectively, which were systematically deprotected to targets 1-3.

  描述了合成核心-2分支四糖 1-3，其中在半乳糖残基的 3 位或 4 位上替代了一个氟原子。准备了糖苷亚胺 13 和 19，并用于提供新型糖苷二糖供体 15 和 21。受体 7 与糖苷溴化物 6 的偶联提供了一种二糖，进一步转化为二糖受体 8。受体 14 与供体 13 的偶联，以及受体 20 与供体 19 的偶联，分别提供了二糖，转化为二糖供体 15 和 21。使用供体 9、15 和 21 对受体 8 和 16 进行区域选择性糖苷化，分别提供四糖 10、17 和 22，随后系统性去保护为目标 1-3。
• Chemical synthesis of a hexasaccharide comprising the Lewisx determinant linked β-(1 → 6) to a linear trimannosyl core and the precursor pentasaccharide lacking fucose
  作者：Rakesh K. Jain、Khushi L. Matta

  DOI：10.1016/0008-6215(95)00376-2

  日期：1996.2

  D-mannopyranosyl)-(1-->6)-2,3,4-tri-O-benzyl- alpha-D- mannopyranoside (12) in the presence of NIS-triflic acid to give, after removal of the chloroacetyl group, the key intermediate, benzyl O-(2,3,4-tri-O-acetyl-alpha-D-mannopyranosyl)-(1-->6)-O-(2,3,4-tri-O-ben zyl- beta-D-mannopyranosyl)-(1-->6)-2,3,4-tri-O-benzyl-alpha-D-mannopyranosid e (14). A similar condensation of 6 and 7 with acceptor 14

  将苯基2,3,4-三-O-乙酰基-6-O-氯乙酰基-1-硫代-α，β-甘露吡喃糖苷（5）与苄基O-（2,3,4-三-O-苄基- β-D-甘露吡喃糖基）-（1-> 6）-2,3,4-三-O-苄基-α-D-甘露吡喃糖苷（12）在NIS-三氟甲磺酸存在下除去氯乙酰基，关键中间体，苄基O-（2,3,4-三-O-乙酰基-α-D-甘露吡喃糖基）-（1-> 6）-O-（2,3,4-三-O -苯甲酰基-β-D-甘露吡喃糖基）-（1→6）-2,3,4-三-O-苄基-α-D-甘露吡喃糖苷e（14）。6和7与受体14的类似缩合，然后除去保护基，分别得到16和18。预期这些化合物可用于针对我们目前正在研究的相关合成抗原的抗体的特异性研究。
• Synthesis of α-d-galactopyranosyl-linked oligosaccharides containing the α-Gal → β-Gal → GlcNAc sequence employing methyl-2,3,4,6-tetra-O-(4-methoxybenzyl)-1-thio- β-d-galactopyranoside as an efficient glycosyl donor
  作者：Gurijala V. Reddy、Rakesh K. Jain、Balwinder S. Bhatti、Khushi L. Matta

  DOI：10.1016/0008-6215(94)00153-7

  日期：1994.10

  Synthesis of two trisaccharides and a tetrasaccharide, namely, alpha-Gal-(1-->3)-beta-Gal-(1-->3)-GlcNAc-beta-OBn (6), alpha-Gal-(1-->3)-beta-Gal-(1-->4)-GlcNAc-beta-OBn (9) and alpha-Gal-(1-->3)-beta-Gal-(1-->4)-GlcNAc-beta-(1-->6)-GalNAc- alpha-OBn (19) was accomplished through development and utilization of a key alpha-galactosyl donor, methyl 2,3,4,6-tetra-O-(4- methoxybenzyl)-1-thio-beta-D-galactopyranoside

  合成两个三糖和一个四糖，即alpha-Gal-（1-> 3）-beta-Gal-（1-> 3）-GlcNAc-beta-OBn（6），alpha-Gal-（1- -> 3）-beta-Gal-（1-> 4）-GlcNAc-beta-OBn（9）和alpha-Gal-（1-> 3）-beta-Gal-（1-> 4）- GlcNAc-β-（1-> 6）-GalNAc-α-OBn（19）是通过开发和利用关键的α-半乳糖基供体甲基2,3,4,6-tetra-O-（4-甲氧基苄基）-1-硫代-β-D-吡喃半乳糖苷（1）。
• Synthesis of Fluorinated Mucin Core 2 Branched Oligosaccharides with the Potential of Novel Substrates and Enzyme Inhibitors for Glycosyltransferases and Sulfotransferases
  作者：Jie Xia、Jun Xue、Robert D. Locke、E. V. Chandrasekaran、T. Srikrishnan、Khushi L. Matta

  DOI：10.1021/jo052626j

  日期：2006.5.1

  Syntheses of fluorinated mucin core 2 tri- and tetrasaccharides modified at the C-3 or C-4 position of the pertinent galactose residue are reported. These compounds were used for the study of sialyltransferases and 3-O-sulfotransferases involved in the biosynthesis of O-glycans. Our acceptor substrate specificity studies on three cloned sialyltransferases (Sia-Ts) revealed that a 3- or 4-fluoro substituent in, beta 1,4Gal resulted in poor acceptors for alpha 2,6(N)Sia-T and alpha 2,3(N)Sia-T, whereas 4-fluoro-Gal,beta 1,3GalNAc alpha was a good acceptor for alpha 2,3(O)Sia-T. Uniquely, 4-F-Gal,beta 1,4GlcNAc,beta 1,6(Gal,beta 1,3)GalNAc alpha-OBn was an inhibitor of alpha 2,6(N)Sia-T activity but not alpha 2,3(N)Sia-T activity. Further we found that the activities of only Gal 3-O-sulfotransferases and not sialyltransferases were adversely affected by a C-3 fluoro substituent at the other Gal terminal of mucin core 2. The strategy of building branched mucin core 2 structures by three glycosidation sequence coupling three classes of glycosyl donors with the reactivity-matching acceptors proved to be successful in syntheses of modified mucin-type core structures of O-glycan. The relative poor yields of the glycosylations using fluorinated galactosyl donors indicated that the fluorine modification dramatically decreased the donor reactivity due to electron-withdrawing effect.