methyl 2,6-di-O-benzoyl-β-D-galactopyranoside | 26927-44-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,6-di-O-benzoyl-β-D-galactopyranoside
• 英文别名: Methyl-2,6-di-O-benzoyl-β-D-galactopyranosid；[(2R,3R,4S,5R,6R)-5-benzoyloxy-3,4-dihydroxy-6-methoxyoxan-2-yl]methyl benzoate
• CAS: 26927-44-6；29575-27-7；51996-13-5；88087-63-2；29575-26-6
• 化学式: C₂₁H₂₂O₈
• 分子量: 402.401
• InChiKey: XILYXPMGDAVPPF-BWZHCXAASA-N

物化性质

• 熔点：
  141-142 °C
• 沸点：
  568.8±50.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2,6-di-O-benzoyl-β-D-galactopyranoside 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 15.67h， 生成 β-D-Galp-(1->3)-β-D-Galp-O-CH3
  参考文献：
  名称：

  Porcine liver (2 → 3)-α-sialyltransferase: substrate specificity studies and application of the immobilized enzyme to the synthesis of various sialylated oligosaccharide sequences

  摘要：

  In search of substrate analogues for the porcine liver beta-D-Galp-(1 --> 3)-D-Galp-NAc: CMP-Neu5Ac-(2 --> 3')-alpha-sialyltransferase, three disaccharides beta-D-Galp-(1 --> 3)-beta-D-Galp-O-CH3 (5), beta-D-Galp-(1 --> 3)-beta-D-(2-OAc)-Galp-O-CH3 (7) and beta-D-Galp-(1 --> 3)-beta-D-(2-OAc)-Galp-O-Bn (11) were synthesized and tested with the enzyme. Disaccharide 7 turned out to be a very good substrate allowing a rapid access to the trisaccharide alpha-Neu5Ac-(2 --> 3)-beta-D-Galp-(1 --> 3)-P-D-(2-OAc)-Galp-O-CH3 (13) on a preparative scale using the crude enzyme immobilized on cationic exchanger. Trisaccharide 13 was further exploited, first as a sialyl donor in Trypanosoma cruzi trans-sialidase catalyzed reaction and second through acetolysis reaction as a source for the synthon alpha-Neu5Ac-(2 --> 3)-D-Gal (16). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00043-8
• 作为产物：
  描述：

  甲基-Β-D-吡喃半乳糖苷 在 吡啶 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 34.25h， 生成 methyl 2,6-di-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  半乳糖受体糖基化反应的区域选择性：实验和理论研究。

  摘要：

  区域选择性糖基化允许为寡糖的合成规划更简单的策略，从而减少了使用保护基的需要。为了进一步了解这种区域选择性，我们分析了糖基化反应中2，6-二保护的甲基α-和β-吡喃半乳糖苷衍生物的OH-3和OH-4基团的相对反应性。通过简单的方法有效地制备了糖基受体，并评估了具有不同反应性的糖基供体。由于OH-3基团的赤道取向，实现了对1→3产物的高区域选择性。分子建模方法支持了支持O-3取代的总体趋势，尽管它显示出一些无法解释控制某些受体之间区域选择性差异的微妙因素的能力。然而，可以通过使用本文测定的一些受体在区域上选择性地安装Galp-（β1→3）-Galp连接。

  DOI：

  10.3762/bjoc.15.294

文献信息

• <i>N</i> ‐Acetyl‐5‐ <i>N</i> ,4‐ <i>O</i> ‐oxazolidinone‐Protected Sialyl Sulfoxide: An α‐Selective Sialyl Donor with Tf ₂ O/(Tol) ₂ SO in Dichloromethane
  作者：Zhen‐yuan Gu、Jia‐xin Zhang、Guo‐wen Xing

  DOI：10.1002/asia.201200172

  日期：2012.7

  Sweet as sugar: Sialyl sulfoxide protected by N‐acetyl‐5‐N,4‐O‐oxazolidinone was readily prepared, and its coupling to various sugar acceptors was investigated. When the reaction was promoted by Tf2O/(Tol)2SO, efficient and highly α‐selective sialylation yielded α(2,6), α(2,3), and α(2,4) glycosidic linkages between sialic acid and glucose/glacotose.

  像糖一样甜：很容易制备受N-乙酰基-5- N，4 - O-恶唑烷酮保护的唾液酸亚砜，并研究了它与各种糖受体的偶联作用。当Tf 2 O /（Tol）2 SO促进反应时，有效且高度α-选择性的唾液酸化会产生唾液酸之间的α（2,6），α（2,3）和α（2,4）糖苷键和葡萄糖/半乳糖。
• Regioselective and 1,2-<i>cis</i>-α-Stereoselective Glycosylation Utilizing Glycosyl-Acceptor-Derived Boronic Ester Catalyst
  作者：Akira Nakagawa、Masamichi Tanaka、Shun Hanamura、Daisuke Takahashi、Kazunobu Toshima

  DOI：10.1002/anie.201504182

  日期：2015.9.7

  Regioselective and 1,2‐cis‐α‐stereoselective glycosylations using 1α,2α‐anhydro glycosyl donors and diol glycosyl acceptors in the presence of a glycosyl‐acceptor‐derived boronic ester catalyst. The reactions proceed smoothly to give the corresponding 1,2‐cis‐α‐glycosides with high stereo‐ and regioselectivities in high yields without any further additives under mild reaction conditions. In addition

  在糖基受体衍生的硼酸酯催化剂存在下，使用1α，2α脱水糖基供体和二醇糖基受体进行区域选择性和1,2-顺-α-立体选择性糖基化反应。反应平稳进行，在温和的反应条件下，无需任何其他添加剂，即可高产率获得相应的具有高立体和区域选择性的1,2-顺-α-糖苷。另外，本糖基化方法已成功地应用于异黄酮糖苷的合成。
• Regio- and stereoselective β-mannosylation using a boronic acid catalyst and its application in the synthesis of a tetrasaccharide repeating unit of lipopolysaccharide derived from E. coli O75
  作者：Nobuya Nishi、Junki Nashida、Eisuke Kaji、Daisuke Takahashi、Kazunobu Toshima

  DOI：10.1039/c7cc00269f

  日期：——

  A novel regio- and stereoselective [small beta]-mannosylation using 1,2-anhydromannose and a diol sugar acceptor in the presence of a boronic acid catalyst and its application are reported.

  报道了在硼酸催化剂存在下使用1，2-脱水甘露糖和二醇糖受体的新颖的区域和立体选择性β-甘露糖基化及​​其应用。
• The flexibility of the LeaLex Tumor Associated Antigen central fragment studied by systematic and stochastic searches as well as dynamic simulations
  作者：Trudy A. Jackson、Valerie Robertson、Anne Imberty、France-Isabelle Auzanneau

  DOI：10.1016/j.bmc.2009.01.020

  日期：2009.2

  The solution conformational behavior of the Tumor-Associated Carbohydrate Antigen Le(a)Le(x) central fragment: methyl alpha-L-fucopyranosyl-(1 -> 4)-2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1 -> 3)-beta-D-galactopyranoside was studied using three computational methods: a rigid systematic search as implemented in Sybyl, a stochastic search as implemented in MOE2004, and dynamics simulations using the SANDER module of AMBER9. Our results illustrate the complementarity of these methods to identify energetically relevant conformations and flexible linkages. In particular, the beta-GlcNAc-(1 -> 3)-Gal linkage was shown to be extremely flexible adopting a wide range of orientations around two energy minima. The modeling results were validated by comparison of theoretical distances, derived from the simulations, with experimental measurements obtained from 1D selective ROESY buildup curves on the synthetic fragment. (c) 2009 Elsevier Ltd. All rights reserved.
• Jacobsen, Steffen; Mols, Ole, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1981, vol. 35, # 3, p. 163 - 168
  作者：Jacobsen, Steffen、Mols, Ole

  DOI：——

  日期：——