(2R,3R,4S,5R,6S)-5-Benzyloxy-6-ethylsulfanyl-2-methyl-tetrahydro-pyran-3,4-diol | 438189-31-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6S)-5-Benzyloxy-6-ethylsulfanyl-2-methyl-tetrahydro-pyran-3,4-diol
• 英文别名: Ethyl 2-o-benzyl-6-deoxy-1-thio-beta-d-galactopyranoside；(2R,3R,4S,5R,6S)-6-ethylsulfanyl-2-methyl-5-phenylmethoxyoxane-3,4-diol
• CAS: 438189-31-2
• 化学式: C₁₅H₂₂O₄S
• 分子量: 298.403
• InChiKey: UCCUDOMINFAHCX-NZNQWUEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  84.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6S)-5-Benzyloxy-6-ethylsulfanyl-2-methyl-tetrahydro-pyran-3,4-diol 在 吡啶 、 4-二甲氨基吡啶 、 sodium azide 、 三乙胺 作用下， 生成 Benzoic acid (2R,3R,4S,5R,6S)-3-azido-5-benzyloxy-6-ethylsulfanyl-2-methyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Expanding the Pyrimidine Diphosphosugar Repertoire: The Chemoenzymatic Synthesis of Amino- and Acetamidoglucopyranosyl Derivatives

  摘要：

  The exploitation of a unique thymidylyltransferase (Ep ) allows the rapid syntheses of thymidine and uridine 5'-(aminodeoxy-α-D-hexopyranosyl diphosphates), 5'-(acetamidodeoxy-α-D-hexopyranosyl diphosphates), and even 5'-(aminodideoxy-α-D-hexopyranosyl diphosphates), which are amino analogues of the products from the native reaction of Ep .

  DOI：

  10.1002/1521-3773(20010417)40:8<1502::aid-anie1502>3.0.co;2-k
• 作为产物：
  描述：

  ethyl 2,3,4-tri-O-acetyl-1-thio-β-D-fucopyranoside 在 盐酸 、 甲醇 、 sodium methylate 、 sodium hydride 、 对甲苯磺酸 作用下， 生成 (2R,3R,4S,5R,6S)-5-Benzyloxy-6-ethylsulfanyl-2-methyl-tetrahydro-pyran-3,4-diol
  参考文献：
  名称：

  Expanding the Pyrimidine Diphosphosugar Repertoire: The Chemoenzymatic Synthesis of Amino- and Acetamidoglucopyranosyl Derivatives

  摘要：

  The exploitation of a unique thymidylyltransferase (Ep ) allows the rapid syntheses of thymidine and uridine 5'-(aminodeoxy-α-D-hexopyranosyl diphosphates), 5'-(acetamidodeoxy-α-D-hexopyranosyl diphosphates), and even 5'-(aminodideoxy-α-D-hexopyranosyl diphosphates), which are amino analogues of the products from the native reaction of Ep .

  DOI：

  10.1002/1521-3773(20010417)40:8<1502::aid-anie1502>3.0.co;2-k

文献信息

• Active-site engineering of nucleotidylyltransferases and general enzymatic methods for the synthesis of natural and "unnatural" UDP- and TDP-nucleotide sugars
  申请人：——

  公开号：US20030055235A1

  公开（公告）日：2003-03-20

  The present invention provides mutant nucleotidylyl-transferases, such as E p , having altered substrate specificity; methods for their production; and methods of producing nucleotide sugars, which utilize these nucleotidylyl-transferases. The present invention also provides methods of synthesizing desired nucleotide sugars using natural and/or modified Ep or other nucleotidyltransferases; and nucleotide sugars sythesized by the present methods. The present invention further provides new glycosyl phosphates, and methods for making them.

  本发明提供了一种突变型核苷酸转移酶，如E p ，具有改变的底物特异性；其生产方法；以及利用这些核苷酸转移酶生产核苷酸糖的方法。本发明还提供了使用天然和/或修饰的Ep或其他核苷酸转移酶合成所需的核苷酸糖的方法；以及通过本发明方法合成的核苷酸糖。本发明进一步提供了新的糖基磷酸酯，及其制造方法。
• Active-site engineering of nucleotidylyltransferases and general enzymatic methods for the synthesis of natural and “unnatural” UDP- and TDP-nucleotide sugars
  申请人：Sloan-Kettering Institute for Cancer Research

  公开号：US07122359B2

  公开（公告）日：2006-10-17

  The present invention provides mutant nucleotidylyl-transferases, such as Ep, having altered substrate specificity; methods for their production; and methods of producing nucleotide sugars, which utilize these nucleotidylyl-transferases. The present invention also provides methods of synthesizing desired nucleotide sugars using natural and/or modified Ep or other nucleotidyltransferases; and nucleotide sugars sythesized by the present methods. The present invention further provides new glycosyl phosphates, and methods for making them.

  本发明提供了突变核苷酸转移酶，例如Ep，其底物特异性发生改变；其生产方法；以及利用这些核苷酸转移酶生产核苷酸糖的方法。本发明还提供了利用天然和/或改性的Ep或其他核苷酸转移酶合成所需核苷酸糖的方法；以及由本方法合成的核苷酸糖。本发明还提供了新的糖基磷酸盐，以及制备它们的方法。
• ACTIVE-SITE ENGINEERING OF NUCLEOTIDYLYLTRANSFERASES AND GENERAL ENZYMATIC METHODS FOR THE SYNTHESIS OF NATURAL AND "UNNATURAL" UDP- AND TDP-NUCLEOTIDE SUGARS
  申请人：THORSON Jon

  公开号：US20070178487A1

  公开（公告）日：2007-08-02

  The present invention provides mutant nucleotidylyl-transferases, such as E p , having altered substrate specificity; methods for their production; and methods of producing nucleotide sugars, which utilize these nucleotidylyl-transferases. The present invention also provides methods of synthesizing desired nucleotide sugars using natural and/or modified E p or other nucleotidyltransferases; and nucleotide sugars sythesized by the present methods. The present invention further provides new glycosyl phosphates, and methods for making them.

  本发明提供了突变核苷酸转移酶，例如Ep，具有改变的底物特异性；其生产方法；以及利用这些核苷酸转移酶生产核苷酸糖的方法。本发明还提供了使用天然和/或改性的Epor或其他核苷酸转移酶合成所需核苷酸糖的方法；以及通过本方法合成的核苷酸糖。本发明还提供了新的糖基磷酸酯，以及制备它们的方法。
• US7122359B2
  申请人：——

  公开号：US7122359B2

  公开（公告）日：2006-10-17
• US7906460B2
  申请人：——

  公开号：US7906460B2

  公开（公告）日：2011-03-15