ethyl 2,4,6-tri-O-benzyl-3-deoxy-1-thio-α-D-ribo-hexopyranoside | 167080-45-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2,4,6-tri-O-benzyl-3-deoxy-1-thio-α-D-ribo-hexopyranoside
• 英文别名: ethyl 2,4,6-tri-O-benzyl-3-deoxy-1-thio-β-D-glucopyranoside；Ethyl 2,4,6-tri-o-benzyl-3-deoxy-1-thio-beta-d-glucopyranoside；(2S,3R,5S,6R)-2-ethylsulfanyl-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 167080-45-7
• 化学式: C₂₉H₃₄O₄S
• 分子量: 478.653
• InChiKey: FFDQNYRUFQVIOU-AUAHOFGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2,4,6-tri-O-benzyl-3-deoxy-1-thio-α-D-ribo-hexopyranoside 在 palladium on activated charcoal 、 galactose-1-phosphate thymidylyltransferase N-Iodosuccinamide 、 三氟甲磺酸 、 magnesium 、 氢气 、 碳酸氢钠 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 uridine 5'-(3-deoxy-α-D-glucopyranosyl diphosphate)
  参考文献：
  名称：

  合成天然和“非天然”UDP-和 TDP-核苷酸糖的通用酶法

  摘要：

  DOI：

  10.1021/ja001444y
• 作为产物：
  描述：

  3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 在 吡啶 、 sodium methylate 、 sodium hydride 、 三氟乙酸 、 zinc(II) iodide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 18.0h， 生成 ethyl 2,4,6-tri-O-benzyl-3-deoxy-1-thio-α-D-ribo-hexopyranoside
  参考文献：
  名称：

  合成天然和“非天然”UDP-和 TDP-核苷酸糖的通用酶法

  摘要：

  DOI：

  10.1021/ja001444y

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。
• Synthesis of monodeoxy analogues of the trisaccharide α-d-Glcp-(1→3)-α-d-Manp-(1→2)-α-d-ManpOMe recognised by Calreticulin/Calnexin
  作者：Emiliano Gemma、Martina Lahmann、Stefan Oscarson

  DOI：10.1016/j.carres.2006.03.015

  日期：2006.7

  Six (3,4,4',6',3" or 6")-monodeoxy analogues of the title trisaccharide (1-6) have been prepared utilising monodeoxy monosaccharide precursors. The reducing end deoxy derivatives were synthesised by N-iodosuccinimide/silver trifluoromethanesulfonate (NIS/AgOTf)-promoted couplings of a common disaccharide thioglycoside donor 10 to suitably protected monodeoxy acceptors 9 and 12, affording trisaccharides, which after deprotection yielded target structures 1 and 2. The non-reducing end deoxy derivatives could similarly be produced by halide-assisted glycosylations of a common disaccharide acceptor 17 with monodeoxy glycosyl bromide donors (obtained from thioglycosides 18 and 20) to yield, after removal of protecting groups, target trisaccharides 3 and 4. The analogues with the deoxy function in the middle mannose residue, were obtained through orthogonal halide-assisted coupling of tetrabenzyl-glucopyranosyl bromide to monodeoxy thioglycoside acceptors to give thioglycoside disaccharides, which subsequently were used as donors in NIS/AgOTf-promoted couplings to a common 2-hydroxy-mannose acceptor 15 to afford trisaccharides; deprotection yielded the final target compounds 5 and 6. (c) 2006 Elsevier Ltd. All rights reserved.
• US7122359B2
  申请人：——

  公开号：US7122359B2

  公开（公告）日：2006-10-17