phenyl-3,4-O-diacetyl-2,6-dideoxy-1-thio-α-L-galactopyranoside | 135197-83-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: phenyl-3,4-O-diacetyl-2,6-dideoxy-1-thio-α-L-galactopyranoside
• 英文别名: [(2S,3R,4S,6S)-3-acetyloxy-2-methyl-6-phenylsulfanyloxan-4-yl] acetate
• CAS: 135197-83-0
• 化学式: C₁₆H₂₀O₅S
• 分子量: 324.398
• InChiKey: FRRHXGZIXGLODC-BLQKSXIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl-3,4-O-diacetyl-2,6-dideoxy-1-thio-α-L-galactopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 sodium azide 、 草酰氯 、 3 A molecular sieve 、 水 、 sodium methylate 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.0h， 生成 Acetic acid (2S,3S,4S)-3-azido-6-chloro-2-methyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  糖肽糖基转移酶合成效用的系统研究

  摘要：

  参与细菌次级代谢产物生物合成的糖基转移酶可用于生成生物活性天然产物的糖修饰类似物。一些糖基转移酶具有宽松的底物特异性，并且已经假定滥交是该类的一个特征。作为探索这些酶合成效用计划的一部分，我们使用纯化的酶和化学合成的 TDP β- 分析了将类似的 2-脱氧-L-糖连接到万古霉素型糖肽苷元的糖基转移酶的底物选择性。 2-脱氧-L-糖类似物。我们表明，虽然这些糖肽糖基转移酶中的一些是混杂的，但其他糖肽糖基转移酶只能容忍它们将处理的底物的微小修改。例如，糖基转移酶 GtfC 和 GtfD，分别将 4-epi-L-vancosamine 和 L-vancosamine 转移到万古霉素假糖苷和氯定向素 B 的葡萄糖单元的 C-2，显示出适度放松的供体底物特异性对其天然苷元的糖基化。相比之下，GtfA，一种将 4-epi-L-vancosamine 连接到苄基位置的转移酶，仅利用与其天然 TDP 糖底

  DOI：

  10.1021/ja052945s

文献信息

• Solution and solid-phase formation of glycosidic linkages
  申请人：Trustees of Princeton University

  公开号：US05700916A1

  公开（公告）日：1997-12-23

  The invention relates to methods that permit the rapid construction of oligosaccharides and other glycoconjugates. Methods for forming multiple glycosidic linkages in solution in a single step are disclosed. The invention takes advantage of the discovery that the relative reactivity of glycoside residues containing anomeric sulfoxides and nucleophilic functional groups can be controlled. In another aspect of the invention, the reactivity of activated anomeric sugar sulfoxides is utilized in a solid phase method for the formation of glycosidic linkages. The methods disclosed may be applied to the preparation of specific oligosaccharides and other glycoconjugates, as well as to the preparation of glycosidic libraries comprising mixtures of various oligosaccharides, including glycoconjugates, which can be screened for biological activity.

  本发明涉及一种可快速构建寡糖和其他糖蛋白的方法。公开了在溶液中一步形成多个糖苷键的方法。本发明利用了发现含有缩醛亚磺酰基和亲核官能团的糖苷残基的相对反应性可以被控制的发现。在本发明的另一个方面中，利用活化的缩醛亚磺酰基糖的反应性，用于固相法形成糖苷键。所公开的方法可应用于特定寡糖和其他糖蛋白的制备，以及制备包含各种寡糖的糖苷库，包括糖蛋白，可用于生物活性筛选。
• Method of forming multiple glycosidic linkages in a single step
  申请人：The Trustees of Princeton University

  公开号：US05635612A1

  公开（公告）日：1997-06-03

  The invention relates to methods that permit the rapid construction of oligosaccharides and other glycoconjugates. Methods for forming multiple glycosidic linkages in solution in a single step are disclosed. The invention takes advantage of the discovery that the relative reactivity of glycoside residues containing anomeric sulfoxides and nucleophilic functional groups can be controlled. In another aspect of the invention, the reactivity of activated anomeric sugar sulfoxides is utilized in a solid phase method for the formation of glycosidic linkages. The methods disclosed may be applied to the preparation of specific oligosaccharides and other glycoconjugates, as well as to the preparation of glycosidic libraries comprising mixtures of various oligosaccharides, including glycoconjugates, which can be screened for biological activity.

  本发明涉及一种快速构建寡糖和其他糖蛋白的方法。揭示了在单步溶液中形成多个糖苷键的方法。本发明利用了发现的含有异构亚磺酰基和亲核官能团的糖苷残基的相对反应性可以被控制的特性。在本发明的另一个方面，利用激活的异构糖亚磺酰基的反应性，用于形成糖苷键的固相方法。所揭示的方法可以应用于特定寡糖和其他糖蛋白的制备，以及制备包含各种寡糖的混合物的糖苷库，包括糖蛋白，可以用于生物活性筛选。
• Recent advances in the synthesis of 2-deoxy-glycosides
  作者：Dianjie Hou、Todd L. Lowary

  DOI：10.1016/j.carres.2009.07.013

  日期：2009.10

  Glycosides of 2-deoxy-sugars, monosaccharides in which the hydroxyl group at C-2 is replaced with a hydrogen atom, occur widely in natural products and therefore have been the subject of intense synthetic activity. The report summarizes recent advances in this area, with a particular focus on work published since an earlier review on the topic, in 2000 (Marzabadi, C. H.: Franck, R. W. Tetrahedron 2000, 56, 8385-8417). (C) 2009 Elsevier Ltd. All rights reserved.
• Anomeric activation of thioglycosides and preparation of deoxyglycosides using polymer-bound iodate(I) complexes
  作者：Janis Jaunzems、Georgia Sourkouni-Argirusi、Martin Jesberger、Andreas Kirschning

  DOI：10.1016/s0040-4039(02)02708-9

  日期：2003.1

  New thiophilic polymer-bound haloate(l) complexes are presented which are well suited for the polymer-assisted solution-phase activation of 2-deoxythioglycosides. In the presence of alcohols 2-deoxyglycosides are obtained in yields between 60 and 95%. Isolation of the target glycosides is further simplified by removing the byproduct diphenyldisulfide by reductive work-up. Here also a polymer-bound reagent, namely borohydride exchange resin, served as a tool for sequestering the sulfur-containing impurities. (C) 2003 Elsevier Science Ltd. All rights reserved.
• SOLUTION AND SOLID-PHASE FORMATION OF GLYCOSIDIC LINKAGES
  申请人：THE TRUSTEES OF PRINCETON UNIVERSITY

  公开号：EP0686160A1

  公开（公告）日：1995-12-13