p-Nitrophenyl 2,3,6-tri-O-benzoyl-β-D-galactopyranoside | 643758-55-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-Nitrophenyl 2,3,6-tri-O-benzoyl-β-D-galactopyranoside
• 英文别名: p-Nitrophenyl 2,3,6-tri-O-benzoyl-beta-D-galactopyranoside；[(2R,3S,4S,5R,6S)-4,5-dibenzoyloxy-3-hydroxy-6-(4-nitrophenoxy)oxan-2-yl]methyl benzoate
• CAS: 643758-55-8
• 化学式: C₃₃H₂₇NO₁₁
• 分子量: 613.577
• InChiKey: CFXBUZCPZDPNFN-SMWBDTCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  163
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  p-Nitrophenyl 2,3,6-tri-O-benzoyl-β-D-galactopyranoside 、 potassium thioacetate 在 吡啶 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以59%的产率得到
  参考文献：
  名称：

  通过多种脱氧硫代糖的水性 S-糖基化简化硫代低聚糖的迭代组装

  摘要：

  一步一步：在水溶液中开发了S-低聚糖的简化实用迭代合成，无需保护任何羟基。可以有效地制备各种脱氧硫代糖结构单元。 Ca(OH) 2 -促进的水性S-糖基化可以以高化学选择性和立体选择性实现。

  DOI：

  10.1002/cssc.202102483
• 作为产物：
  描述：

  苯甲酰氯 、 4-硝基苯基-D-吡喃葡糖苷 在 吡啶 作用下， 以58%的产率得到p-Nitrophenyl 2,3,6-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  通过多种脱氧硫代糖的水性 S-糖基化简化硫代低聚糖的迭代组装

  摘要：

  一步一步：在水溶液中开发了S-低聚糖的简化实用迭代合成，无需保护任何羟基。可以有效地制备各种脱氧硫代糖结构单元。 Ca(OH) 2 -促进的水性S-糖基化可以以高化学选择性和立体选择性实现。

  DOI：

  10.1002/cssc.202102483

文献信息

• Engineered enzymes and their use for synthesis of thioglycosides
  申请人：Withers G Stephen

  公开号：US20060035342A1

  公开（公告）日：2006-02-16

  Mutant glycosidases in which the amino acid in the active site that serves as the acid, base or acid/base-catalyst is converted from a carboxylic acid to some other amino acid (for example to a simple alkyl, as in alanine or glycine) can catalyze the reaction of a thiosugar acceptor and an activated donor to form a thioglycoside. The “thioglycoligases” represent a novel class of mutant enzymes, and represent a first aspect of the invention. Thioglycoligases can be used in accordance with the method of the invention to couple a thiosugar acceptor and an activated donor to form a thioglycoside. By selection of the donor and acceptor species, as well as the specific enzyme employed, thioglycosides of different structure and stereochemistry can be obtained.

  突变的糖苷酶中，活性位点中作为酸、碱或酸碱催化剂的氨基酸从羧酸转变为其他氨基酸（例如转变为简单的烷基，如丙氨酸或甘氨酸），可以催化硫代糖受体和活化供体的反应，形成硫代糖苷。 "硫代糖聚合酶"代表一类新型突变酶，并代表本发明的第一个方面。可以根据本发明的方法使用硫代糖聚合酶将硫代糖受体和活化供体偶联形成硫代糖苷。通过选择供体和受体物种以及特定的酶，可以获得不同结构和立体化学的硫代糖苷。
• Engineered Enzymes and Their Use for Synthesis of Thioglycosides
  申请人：Withers G. Stephen

  公开号：US20070004010A1

  公开（公告）日：2007-01-04

  Mutant glycosidases in which the amino acid in the active site that serves as the acid, base or acid/base-catalyst is converted from a carboxylic acid to some other amino acid (for example to a simple alkyl, as in alanine or glycine) can catalyze the reaction of a thiosugar acceptor and an activated donor to form a thioglycoside. The “thioglycoligases” represent a novel class of mutant enzymes, and represent a first aspect of the invention. Thioglycoligases can be used in accordance with the method of the invention to couple a thiosugar acceptor and an activated donor to form a thioglycoside. By selection of the donor and acceptor species, as well as the specific enzyme employed, thioglycosides of different structure and stereochemistry can be obtained.

  突变的糖苷酶中，活性位点中作为酸、碱或酸碱催化剂的氨基酸从羧酸转变为其他氨基酸（例如转变为简单的烷基，如丙氨酸或甘氨酸），可以催化硫代糖受体和活化供体的反应形成硫代糖苷。这些“硫代糖合酶”代表了突变酶的一类新型酶，也代表了本发明的第一个方面。可以根据本方法使用硫代糖受体和活化供体耦合形成硫代糖苷。通过选择供体和受体物种以及具体的酶，可以获得不同结构和立体化学的硫代糖苷。
• [EN] ENGINEERED ENZYMES AND THEIR USE FOR SYNTHESIS OF THIOGLYCOSIDES<br/>[FR] ENZYMES MODIFIEES ET LEUR UTILISATION POUR LA SYNTHESE DE THIOGLYCOSIDES
  申请人：UNIV BRITISH COLUMBIA

  公开号：WO2004024908A1

  公开（公告）日：2004-03-25

  Mutant glycosidases in which the amino acid in the active site that serves as the acid, base or acid/base-catalyst is converted from a carboxylic acid to some other amino acid (for example to a simple alkyl, as in alanine or glycine) can catalyze the reaction of a thiosugar acceptor and an activated donor to form a thioglycoside. The 'thioglycoligases' represent a novel class of mutant enzymes, and represent a first aspect of the invention. Thioglycoligases can be used in accordance with the method of the invention to couple a thiosugar acceptor and an activated donor to form a thioglycoside. By selection of the donor and acceptor species, as well as the specific enzyme employed, thioglycosides of different structure and stereochemistry can be obtained.
• Streamlined Iterative Assembly of Thio‐Oligosaccharides by Aqueous <i>S</i> ‐Glycosylation of Diverse Deoxythio Sugars
  作者：Peng Wen、Peijing Jia、Qiuhua Fan、Bethany J. McCarty、Weiping Tang

  DOI：10.1002/cssc.202102483

  日期：2022.2.8

  Step by step: A streamlined practical iterative synthesis of S-oligosaccharides is developed in aqueous solution without the need of protecting any of the hydroxy groups. Various deoxythio sugar building blocks can be prepared efficiently. The Ca(OH)2-promoted aqueous S-glycosylation can be realized with high chemo- and stereoselectivity.

  一步一步：在水溶液中开发了S-低聚糖的简化实用迭代合成，无需保护任何羟基。可以有效地制备各种脱氧硫代糖结构单元。 Ca(OH) 2 -促进的水性S-糖基化可以以高化学选择性和立体选择性实现。