methyl 6-O-benzoyl-2,3-di-O-benzyl-β-D-glucopyranoside | 31873-35-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-benzoyl-2,3-di-O-benzyl-β-D-glucopyranoside
• 英文别名: methyl 2,3-di-O-benzyl-6-O-benzoyl-β-D-glucopyranoside；[(2R,3R,4S,5R,6R)-3-hydroxy-6-methoxy-4,5-bis(phenylmethoxy)oxan-2-yl]methyl benzoate
• CAS: 31873-35-5
• 化学式: C₂₈H₃₀O₇
• 分子量: 478.542
• InChiKey: GAFQPRARNIDGOF-JBMSBTKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 6-O-benzoyl-2,3-di-O-benzyl-β-D-glucopyranoside 在 palladium dichloride 吡啶 、 Amberlite A-26-F (3.5 meq. of F(-)/g) 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 苯 为溶剂， 反应 12.0h， 生成 甲基 4-脱氧-4-氟-D-吡喃半乳糖苷
  参考文献：
  名称：

  Preparation of two methyl deoxyfluoro-β-d-galactopyranosides, and their interaction with galactan-specific immunoglobulin A 1539 (fab′)

  摘要：

  Methyl 2-deoxy-2-fluoro-beta-D-glactopyranoside (2) and methyl 4-deoxy-4-fluoro-beta-D-glactopyranoside (7) have been prepared, and the possibility of their binding to (1 leads to 6)-beta-D-galactopyranan-specific immunoglobulin A J539 (Fab') has been investigated. Compound 2 does not show binding, whereas 7 does. It appears that the 2-hydroxyl group of methyl beta-D-galactopyranoside may take part in hydrogen bonding to the protein.

  DOI：

  10.1016/s0008-6215(00)85575-5
• 作为产物：
  描述：

  methyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 在 吡啶 作用下， 以 水 为溶剂， 生成 methyl 6-O-benzoyl-2,3-di-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Preparation of two methyl deoxyfluoro-β-d-galactopyranosides, and their interaction with galactan-specific immunoglobulin A 1539 (fab′)

  摘要：

  Methyl 2-deoxy-2-fluoro-beta-D-glactopyranoside (2) and methyl 4-deoxy-4-fluoro-beta-D-glactopyranoside (7) have been prepared, and the possibility of their binding to (1 leads to 6)-beta-D-galactopyranan-specific immunoglobulin A J539 (Fab') has been investigated. Compound 2 does not show binding, whereas 7 does. It appears that the 2-hydroxyl group of methyl beta-D-galactopyranoside may take part in hydrogen bonding to the protein.

  DOI：

  10.1016/s0008-6215(00)85575-5

文献信息

• Regioselective Benzoylation of Diols and Carbohydrates by Catalytic Amounts of Organobase
  作者：Yuchao Lu、Chenxi Hou、Jingli Ren、Xiaoting Xin、Hengfu Xu、Yuxin Pei、Hai Dong、Zhichao Pei

  DOI：10.3390/molecules21050641

  日期：——

  A novel metal-free organobase-catalyzed regioselective benzoylation of diols and carbohydrates has been developed. Treatment of diol and carbohydrate substrates with 1.1 equiv. of 1-benzoylimidazole and 0.2 equiv. of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in MeCN under mild conditions resulted in highly regioselective benzoylation for the primary hydroxyl group. Importantly, compared to most commonly

  已经开发出一种新型的无金属有机碱催化的二醇和碳水化合物的区域选择性苯甲酰化。用 1.1 当量处理二醇和碳水化合物底物。1-苯甲酰咪唑和 0.2 当量。1,8-二氮杂双环[5.4.0] undec-7-ene (DBU) 在温和条件下在 MeCN 中的反应导致伯羟基的高度区域选择性苯甲酰化。重要的是，与最常用的伯羟基保护基团相比，苯甲酰基保护基团提供了一种新的保护策略。
• Stannous chloride as a low toxicity and extremely cheap catalyst for regio-/site-selective acylation with unusually broad substrate scope
  作者：Jian Lv、Jian-Cheng Yu、Guang-Jing Feng、Tao Luo、Hai Dong

  DOI：10.1039/d0gc02739a

  日期：——

  containing cis-vicinal diol, the substrate scope also includes glycosides without cis-vicinal diol. For such a substrate scope, usually, only methods using stoichiometric amounts of organotin reagents can lead to the same protection pattern with high selectivities and highly isolated yields (84–97% in most cases). Therefore, SnCl2, as a low toxicity and extremely cheap reagent, should be the best catalyst

  这项工作报告了氯化亚锡（SnCl 2）催化的区域/位点选择性酰化反应，其底物范围异常广泛。除了含有顺式-邻位二醇的1,2-和1,3-二醇和糖苷外，底物范围还包括不含顺式-邻位二醇的糖苷。对于这种底物范围，通常，只有使用化学计量的有机锡试剂的方法才能以高选择性和高分离产率（大多数情况下为84–97％）产生相同的保护模式。因此，与以前报道的任何试剂相比，SnCl 2作为一种低毒且极其便宜的试剂，应该是区域/位点选择性酰化反应的最佳催化剂。
• Mapping the Relationship between Glycosyl Acceptor Reactivity and Glycosylation Stereoselectivity
  作者：Stefan van der Vorm、Jacob M. A. van Hengst、Marloes Bakker、Herman S. Overkleeft、Gijsbert A. van der Marel、Jeroen D. C. Codée

  DOI：10.1002/anie.201802899

  日期：2018.7.2

  The reactivity of both coupling partners—the glycosyl donor and acceptor—is decisive for the outcome of a glycosylation reaction, in terms of both yield and stereoselectivity. Where the reactivity of glycosyl donors is well understood and can be controlled through manipulation of the functional/protecting‐group pattern, the reactivity of glycosyl acceptor alcohols is poorly understood. We here present

  就产量和立体选择性而言，两个偶联伙伴（糖基供体和受体）的反应性对糖基化反应的结果都具有决定性作用。如果对糖基供体的反应性了解得很好，并且可以通过功能/保护基团模式的控制来控制，则对糖基受体醇的反应性了解得很少。我们在这里提出了一个操作简单的系统来评估糖基受体的反应性，该系统采用了两个构象锁定的供体，其立体选择性严格取决于亲核试剂的反应性。筛选了大量受体，并建立了它们的结构-反应性/立体选择性关系。通过系统地改变保护基，可以调节糖基受体的反应性以获得立体选择性。顺式葡萄糖基化。
• A green and convenient method for regioselective mono and multiple benzoylation of diols and polyols
  作者：Xiaoling Zhang、Bo Ren、Jiantao Ge、Zhichao Pei、Hai Dong

  DOI：10.1016/j.tet.2015.12.074

  日期：2016.2

  An efficient method for regioselective benzoylation of diols and polyols was developed. The benzoylation is catalyzed by only 0.2 equiv of benzoate anion in acetonitrile with the addition of a stoichiometric amount of benzoic anhydride under very mild condition, leading to high yields. Compared with all other methods, this method shows particular advantage in regioselective multiple benzoylation of polyols, and in avoiding the use of any metal-based catalysts and any amine bases, which is more environment friendly. (C) 2015 Elsevier Ltd. All rights reserved.
• OSCARSON, STEFAN;SZONYI, MARIA, J. CARBOHYDR. CHEM., 8,(1989) N, C. 663-668
  作者：OSCARSON, STEFAN、SZONYI, MARIA

  DOI：——

  日期：——