methyl 2-O-benzyl-β-D-xylopyranoside | 51755-03-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-benzyl-β-D-xylopyranoside
• 英文别名: Methyl-2-O-benzyl-β-D-xylopyranosid；Methyl 2-O-benzyl-beta-D-xylopyranoside；(3R,4S,5R,6R)-6-methoxy-5-phenylmethoxyoxane-3,4-diol
• CAS: 51755-03-4
• 化学式: C₁₃H₁₈O₅
• 分子量: 254.283
• InChiKey: IYWFAMRXAHEYTQ-YVECIDJPSA-N

物化性质

• 沸点：
  406.4±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-O-benzyl-β-D-xylopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 3.5h， 生成 methyl 3,4-di-O-benzoyl-β-D-xylopyranoside
  参考文献：
  名称：

  Petrakova, Eva; Schraml, Jan, Collection of Czechoslovak Chemical Communications, 1983, vol. 48, # 3, p. 877 - 888

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-xylopyranoside 在 四丁基氟化铵 、 溶剂黄146 、 silver(l) oxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 methyl 2-O-benzyl-β-D-xylopyranoside
  参考文献：
  名称：

  Catalytic Site-Selective Acylation of Carbohydrates Directed by Cation–n Interaction

  摘要：

  Site-selective functionalization of hydroxyl groups in carbohydrates is one of the long-standing challenges in chemistry. Using a pair of chiral catalysts, we now can differentiate the most prevalent trans-1,2-diols in pyranoses systematically and predictably. Density functional theory (DFT) calculations indicate that the key determining factor for the selectivity is the presence or absence of a cation-n interaction between the cation in the acylated catalyst and an appropriate lone pair in the substrate. DFT calculations also provided a predictive model for site-selectivity and this model is validated by various substrates.

  DOI：

  10.1021/jacs.7b01412

文献信息

• A Chiral Copper Catalyzed Site‐Selective O‐Alkylation of Carbohydrates
  作者：Bo Ren、Jiaxi Wang、Mengyao Zhang、Yue Chen、Wei Zhao

  DOI：10.1002/adsc.202101121

  日期：2022.2

  Highly regioselective alkylation of sugar hydroxyl groups has always been an important challenge in carbohydrate chemistry, especially for the selective alkylation of trans diols, there is no direct and efficient catalytic method so far. A chiral copper catalyzed universal highly site-selective alkylation of trans-diols method is realized. This reaction is performed under mild conditions and has broad

  糖羟基的高度区域选择性烷基化一直是碳水化合物化学中的一个重要挑战，尤其是反式二醇的选择性烷基化，目前还没有直接有效的催化方法。实现了一种手性铜催化的反式二醇通用高位点选择性烷基化方法。该反应条件温和，底物范围广。反应的选择性可以通过调节铜试剂和手性配体来控制。该方法也应用于药物和天然产物的位点选择性修饰。
• Tin-Mediated Regioselective Benzylation and Allylation of Polyols: Applicability of a Catalytic Approach Under Solvent-Free Conditions
  作者：Maddalena Giordano、Alfonso Iadonisi

  DOI：10.1021/jo402399n

  日期：2014.1.3

  The first catalytic version of the stannylene-mediated benzylation and allylation of polyols is reported. The methodology is based on a simple solvent-free protocol that significantly advances, in terms of both experimental ease and synthetic scope, the applicability of tin-promoted selective protections. The described approach is indeed endowed with a very large number of advantages over routine protocols:

  报道了由亚苯乙烯介导的多元醇的苄基化和烯丙基化的第一个催化形式。该方法基于简单的无溶剂方案，在实验简便性和合成范围方面，都大大提高了锡促进的选择性保护的适用性。与常规方案相比，所描述的方法确实具有许多优点：使用低催化负载量的廉价Bu 2SnO是避免使用溶剂的一步法工艺，是在空气中进行反应的最低要求的实验程序，缩短了反应时间，简化了后处理工艺，目标范围广，在许多情况下，收率均优于常规协议。另外，无催化溶剂的方法将亚锡烷基化学的范围扩展到了空前的应用领域，以还原糖和合成高苄基化的结构单元，而这些过程可以通过更苛刻的程序来获得。从概念的角度来看，所描述的结果表明，无溶剂条件可以帮助开发催化方法，否则该方法在溶液中无效。
• Haque, Mohammed Ekramul; Kikuchi, Tohru; Yoshimoto, Kimihiro, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 6, p. 2243 - 2255
  作者：Haque, Mohammed Ekramul、Kikuchi, Tohru、Yoshimoto, Kimihiro、Tsuda, Yoshisuke

  DOI：——

  日期：——
• Schraml, Jan; Petrakova, Eva; Pihar, Otomar, Collection of Czechoslovak Chemical Communications, 1983, vol. 48, # 7, p. 1829 - 1841
  作者：Schraml, Jan、Petrakova, Eva、Pihar, Otomar、Hirsch, Jan、Chvalovsky, Vaclav

  DOI：——

  日期：——
• Catalytic Site-Selective Acylation of Carbohydrates Directed by Cation–<i>n</i> Interaction
  作者：Guozhi Xiao、Gabriel A. Cintron-Rosado、Daniel A. Glazier、Bao-min Xi、Can Liu、Peng Liu、Weiping Tang

  DOI：10.1021/jacs.7b01412

  日期：2017.3.29

  Site-selective functionalization of hydroxyl groups in carbohydrates is one of the long-standing challenges in chemistry. Using a pair of chiral catalysts, we now can differentiate the most prevalent trans-1,2-diols in pyranoses systematically and predictably. Density functional theory (DFT) calculations indicate that the key determining factor for the selectivity is the presence or absence of a cation-n interaction between the cation in the acylated catalyst and an appropriate lone pair in the substrate. DFT calculations also provided a predictive model for site-selectivity and this model is validated by various substrates.