3,4,6-tri-O-acetyl-2-deoxy-2-formamido-α-D-glucopyranosyl chloride | 125084-87-9

• 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: 3,4,6-tri-O-acetyl-2-deoxy-2-formamido-α-D-glucopyranosyl chloride
• 英文别名: [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-6-chloro-5-formamidooxan-2-yl]methyl acetate
• CAS: 125084-87-9
• 化学式: C₁₃H₁₈ClNO₈
• 分子量: 351.741
• InChiKey: KEEAMFRGDLFDFQ-VEGXAWMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-formamido-α-D-glucopyranosyl chloride 在 4 A molecular sieve 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 三正丁基氢锡 、 silver trifluoromethanesulfonate 、 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.17h， 生成 1,2:3,4-di-O-isopropylidene-6-O-(3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-hexopyranosyl)-α-D-galactopyranose
  参考文献：
  名称：

  The synthesis of 2′-deoxy-β-disaccharides: Novel approaches

  摘要：

  DOI：

  10.1016/0008-6215(89)85044-x
• 作为产物：
  描述：

  1,3,4,6-Tetra-O-acetyl-2-desoxy-2-formamido-β-D-glucose 在 盐酸 作用下， 以 various solvent(s) 为溶剂， 以80%的产率得到3,4,6-tri-O-acetyl-2-deoxy-2-formamido-α-D-glucopyranosyl chloride
  参考文献：
  名称：

  The synthesis of 2′-deoxy-β-disaccharides: Novel approaches

  摘要：

  DOI：

  10.1016/0008-6215(89)85044-x

文献信息

• Hydrolytic and transglycosylation reactions of N-acyl modified substrates catalysed by β-N-acetylhexosaminidases
  作者：Pavla Fialová、Lenka Weignerová、Jana Rauvolfová、Věra Přikrylová、Andrea Pišvejcová、Rüdiger Ettrich、Marek Kuzma、Petr Sedmera、Vladimı́r Křen

  DOI：10.1016/j.tet.2003.10.111

  日期：2004.1

  hydrolytic and transglycosylation capabilities of 35 fungal β-N-acetylhexosaminidases with p-nitrophenyl 2-amino-2-deoxy-β-d-glucopyranoside and its four N-acyl derivatives (CHO, COCH2OH, COCH2CH3, COCF3) as substrates were tested. The preparation of four novel p-nitrophenyl disaccharides from these unnatural substrates catalysed by enzymes from Aspergillus oryzae, Penicillium oxalicum and Talaromyces flavus

  35种真菌β- N-乙酰基己糖胺酶与对硝基苯基2-氨基-2-脱氧-β-d-吡喃葡萄糖苷及其4种N-酰基衍生物（CHO，COCH 2 OH，COCH 2 CH 3的水解和转糖基化能力），COCF 3）作为底物进行了测试。的四种新型制备p硝基苯基二糖从由酶催化的这些非天然底物的米曲霉，草酸青霉和踝节菌属菌代表了相当大的扩展糖苷酶的合成潜力。
• Phosphorylase-catalyzed N-formyl-α-glucosaminylation of maltooligosaccharides
  作者：Satoshi Kawazoe、Hironori Izawa、Mutsuki Nawaji、Yoshiro Kaneko、Jun-ichi Kadokawa

  DOI：10.1016/j.carres.2010.01.001

  日期：2010.3

  This paper describes the phosphorylase-catalyzed enzymatic N-formyl-alpha-glucosaminylation of maltooligosaccharides for direct incorporation of 2-deoxy-2-formamido-alpha-D-glucopyranose units into maltooligosaccharides. When the reaction of 2-deoxy-2-formamido-alpha-D-glucopyranose-1-phosphate (GlcNF-1-P) as the glycosyl donor and maltotetraose as a glycosyl acceptor was performed in the presence of phosphorylase, the N-formyl-alpha-D-glucosaminylated pentasaccharide was produced, as confirmed by MALDI-TOF MS. Furthermore, the glucoamylase-catalyzed reaction of the crude products supported that the 2-deoxy-2-formamido-alpha-D-glucopyranoside unit was positioned at the non-reducing end of the pentasaccharide. The pentasaccharide was isolated from the crude products and its structure was further determined by the (1)H NMR analysis. On the other hand, when the phosphorylase-catalyzed reactions of maltotriose and maltopentaose using GlcNF-1-P were conducted, no N-formyl-alpha-glucosaminylation took place in the former system, whereas the latter system gave N-formyl-alpha-D-glucosaminylated oligosaccharides with various degrees of polymerization. These results could be explained by the recognition behavior of phosphorylase toward maltooligosaccharides. (C) 2010 Elsevier Ltd. All rights reserved.
• Glycosylations with N-formylamino sugars: A new approach to 2′-deoxy-β-disaccharides
  作者：Paolo Tavecchia、Michel Trumtel、Alain Veyrières、Pierre Sinay

  DOI：10.1016/s0040-4039(01)80443-3

  日期：1989.1
• TAVECCHIA, PAOLO;TRUMTEL, MICHEL;VEYRIERES, ALAIN;SINAY, PIERRE, TETRAHEDRON LETT., 30,(1989) N9, C. 2533-2536
  作者：TAVECCHIA, PAOLO、TRUMTEL, MICHEL、VEYRIERES, ALAIN、SINAY, PIERRE

  DOI：——

  日期：——