ethyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-1-thio-β-D-glucopyranoside | 345197-20-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: ethyl 6-azido-2,3,4-tri-O-acetyl-6-deoxy-1-thio-β-D-glucopyranoside；[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-2-(azidomethyl)-6-ethylsulfanyloxan-3-yl] acetate
• CAS: 345197-20-8
• 化学式: C₁₄H₂₁N₃O₇S
• 分子量: 375.403
• InChiKey: ZGUPGPYAGMWQEG-RGDJUOJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ethyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-1-thio-β-D-glucopyranoside 在 吡啶 、 sodium methylate 、 sodium hydride 、 苯硫酚 、 三乙胺 、 tin(ll) chloride 作用下， 生成 Ethyl 6-acetamido-2,3,4-tri-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside
  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-6-O-(p-tolylsulfonyl)-1-thio-β-D-glucopyranoside 在 sodium azide 作用下， 以 丙酮 为溶剂， 反应 22.0h， 以41%的产率得到ethyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  通过点击化学高效合成糖基化天冬酰胺酸结构单元

  摘要：

  铜催化 1完全乙酰化的炔丙基 1-硫糖苷（葡萄糖、半乳糖、甘露糖和鼠李糖系列）和 Fmoc-L-Asp(O-T-Bu)炔丙基酰胺与叔丁基 (S)-4-azido-3 的 ,3-偶极环加成-芴基甲氧基氨基丁酸、2,3,4,6-三-O-乙酰-糖基叠氮化物和乙基 2,3,4-三-O-乙酰-6-叠氮基-6-脱氧-1-硫糖苷（葡萄糖、半乳糖、甘露糖）系列），分别（点击化学）。由此获得的正交保护的L-天冬酰胺酸和(S)-3-氨基丁酸带有乙酰基保护的糖或糖苷部分，通过三唑间隔物连接，是组合糖肽合成的合适构件。

  DOI：

  10.1055/s-2008-1032150

文献信息

• Synthesis of 1,2,3-Triazole-Linked Glycoconjugates of N-(2-Aminoethyl)glycine: Building Blocks for the Construction of Combinatorial Glycopeptide Libraries
  作者：Thomas Ziegler、Kai Günther

  DOI：10.1055/s-0033-1339137

  日期：——

  blocks for the construction of combinatorial glycopeptide libraries. Twenty-nine glycoconjugate building blocks based on the N-(2-aminoethyl)glycine (AEG) backbone and sugars linked to the backbone by a 1,2,3-triazole moiety were prepared via copper-catalyzed 1,3-dipolar cycloaddition of monosaccharides bearing an azide group and N-4-pentynoyl-AEG. The initial glycoconjugates were converted to the corresponding

  摘要 通过N-（2-氨基乙基）甘氨酸（AEG）骨架和通过1,2,3-三唑部分与骨架连接的糖，形成29个糖缀合物结构单元，通过铜催化的1,3-偶极环加成反应制备。带有叠氮基和N -4-戊炔基-AEG的单糖。将最初的糖缀合物分别转化为相应的酸和五氟苯基酯，它们是构建组合糖肽文库的有用组成部分。 通过N-（2-氨基乙基）甘氨酸（AEG）骨架和通过1,2,3-三唑部分与骨架连接的糖，形成29个糖缀合物结构单元，通过铜催化的1,3-偶极环加成反应制备。带有叠氮基和N -4-戊炔基-AEG的单糖。将最初的糖缀合物分别转化为相应的酸和五氟苯基酯，它们是构建组合糖肽文库的有用组成部分。
• Preparation of Some Glycosyl Amino Acid Building Blocks via Click Reaction and Construction of a Glycotetrapeptide Library Using Spot Synthesis
  作者：Kai Günther、Carsten Schips、Thomas Ziegler

  DOI：10.1080/07328300802419873

  日期：2008.12.11

  The copper-catalyzed 1,3-dipolar cycloaddition reaction between ethyl 2,3,4-tri-O- actetyl-6-azido-6-deoxy-1-thio-beta-D-glucopyranoside (2), ethyl 2,3,4-tri-O-actetyl-6-azido-6-deoxy-1-thio-beta-D-galactopyranoside (4), methyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-alpha-D-mannopyranoside (7), and methyl 2,3,6-tri-O-acetyl-2-azido-2-deoxy-beta-D-glucopyranoside (9), and tert-butyl-protected Fmoc-asparaginic acid propargylamide (10) gave the corresponding protected glycosyl amino acid building blocks 11, 13, 15, and 17 in 67% to 95% yield. The latter were converted into the corresponding pentafluorophenyl esters 12, 14, 16, and 18, which were used for a spot synthesis of a combinatorial library containing 256 glycotetrapeptides. The library was screened for lectin-binding affinity with the lectins Concanavalin A (Con A), phaseolus vulgaris (PHA-E), and galantus nivalis (GNA).