phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-glucopyranoside | 158198-55-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-glucopyranoside
• 英文别名: phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-glucopyranose；phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-L-idopyranoside；(2R,3R,4S,5R,6S)-2-(Acetoxymethyl)-4-(benzyloxy)-6-(phenylthio)tetrahydro-2H-pyran-3,5-diyl diacetate；[(2R,3R,4S,5R,6S)-3,5-diacetyloxy-4-phenylmethoxy-6-phenylsulfanyloxan-2-yl]methyl acetate
• CAS: 158198-55-1
• 化学式: C₂₅H₂₈O₈S
• 分子量: 488.559
• InChiKey: DOMAZPUOBHMKAR-RXFVIIJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-glucopyranoside 在 2,6-二甲基吡啶 、 甲醇 、 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 二苯基亚砜 、 sodium methylate 、 2,4,6-三叔丁基嘧啶 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 4.67h， 生成 methyl (benzyl 3-O-benzyl-2,4-O-di-tert-butylsilylene-β-D-glucopyranosyluronate)
  参考文献：
  名称：

  Strict Stereocontrol by 2,4-O-Di-tert-butylsilylene Group on β-Glucuronylations

  摘要：

  Strict beta-controlled glucuronylations without classical neighboring-group participation were achieved by the assistance of a 2,4-O-di-tert-butylsilylene group. Comparison of activation conditions and conformational analysis indicated that the strict beta-selectivity was achieved by steric hindrance of the 2,4-O-di-tert-butylsilylene group and not by complex glycosyl intermediates.

  DOI：

  10.1021/ol300634x
• 作为产物：
  描述：

  benzyl-O-β-D-glucopyranoside 在 三氟化硼乙醚 、 sodium acetate 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  First Synthesis of a Trisaccharide of Glycosylkaemferide: A Resistance Factor in Carnations

  摘要：

  A trisaccharide, phenyl beta-D-glucopyranosyl-(1 --> 2)-[alpha-L-rhamnopyranosyl-(1 --> 6)]-1-thio-beta-D-glucopyranoside, of glycosylkaemferide, a resistance factor in carnations, was synthesized in a practical way.

  DOI：

  10.1081/scc-120027259

文献信息

• A Modular Strategy Toward the Synthesis of Heparin-like Oligosaccharides Using Monomeric Building Blocks in a Sequential Glycosylation Strategy
  作者：Jeroen D. C. Codée、Bas Stubba、Marialuisa Schiattarella、Herman S. Overkleeft、Constant A. A. van Boeckel、Jacques H. van Boom、Gijsbert A. van der Marel

  DOI：10.1021/ja045613g

  日期：2005.3.1

  A novel flexible assembly strategy is described for the modular synthesis of heparin and heparan sulfates. The reported strategy uses monomeric building blocks to construct the oligosaccharide chain to attain a maximum degree of flexibility. In the assembly, 1-hydroxyl glucosazido- and 1-thio uronic acid donors are combined in a sequential glycosylation protocol using sulfonium triflate activator systems

  描述了一种新的灵活组装策略，用于肝素和硫酸乙酰肝素的模块化合成。报道的策略使用单体构建块来构建寡糖链以获得最大程度的灵活性。在组装中，使用三氟甲磺酸锍激活剂系统将 1-羟基葡糖叠氮基和 1-硫代糖醛酸供体结合在连续糖基化方案中。关键的 1-硫代糖醛酸是以有效的方式从双丙酮葡萄糖中获得的，采用部分保护的葡萄糖和艾糖硫糖苷的化学和区域选择性氧化。
• Synthesis of Kojidextrins and Their Protein Conjugates. Incidence of Steric Mismatch in Oligosaccharide Synthesis
  作者：Vince Pozsgay、Eric P. Dubois、Lewis Pannell

  DOI：10.1021/jo962300y

  日期：1997.5.1

  Kojidextrins are biologically important oligosaccharides that are involved in many physiological processes including protein glycosylation and bacterial growth. As part of our project to explore the role kojidextrins may play in bacterial pathogenesis, here we report Synthetic routes to kojibiose (54), -triose (58), -tetraose (64), and -pentaose (69) equipped with alpha-linked (hydrazinocarbonyl)-pentyl aglycon, using linear and convergent strategies. In the search for a rapid convergent strategy for the construction of extended kojidextrins, four kojibiose donors (1-4) were synthesized that contain acyl- and ether-type protecting groups in various ratios. These were tested to probe the influence of diverse protecting group assemblies on their glycosyl donor ability. Attempted condensation of these donors with kojitriose and -tetraose accepters failed to give the desired products apparently because of steric mismatch between the donor and the acceptor moieties. A one-pot procedure was developed for the covalent attachment of the synthetic saccharides through their hydrazido group to human serum albumin (HSA) using Tietze's squarate method to give neoglycoproteins containing up to 28 saccharide units per HSA.
• Synthesis of 2-acetamido-2-deoxy-β-d-glucopyranosyl-(1 → 2)-α-d-mannopyranosyl (1 → 6)-β-d-mannopyranosyl-(1 → 4)-2-acetamido-2-deoxy-d-glucopyranose. Acceptor-substrate recognition by N-acetylglucosaminyltransferase-V (GnT-V)
  作者：Shaheer H. Khan、Khushi L. Matta

  DOI：10.1016/0008-6215(95)00257-x

  日期：1995.12