dimeric 3,4,6-tri-O-acetyl-2-deoxy-2-nitroso-α-D-glucopyranosyl chloride | 48192-76-3

• 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: dimeric 3,4,6-tri-O-acetyl-2-deoxy-2-nitroso-α-D-glucopyranosyl chloride
• 英文别名: 3,4,6-tri-O-acetyl-2-deoxy-2-nitroso-α-D-glucopyranosyl chloride；3,4,6-Tri-O-acetyl-2-nitroso-2-desoxy-α-D-glucopyranosylchlorid；[(2R,3S,4R,5R,6R)-3,4-diacetyloxy-6-chloro-5-nitrosooxan-2-yl]methyl acetate
• CAS: 48192-76-3
• 化学式: C₁₂H₁₆ClNO₈
• 分子量: 337.714
• InChiKey: KFPZZYYFCIVJOD-OOCWMUITSA-N

物化性质

• 沸点：
  417.7±45.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  dimeric 3,4,6-tri-O-acetyl-2-deoxy-2-nitroso-α-D-glucopyranosyl chloride 在 吡啶 、 硼烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 168.08h， 生成 [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-amino-6-(4-methyl-2-oxochromen-7-yl)oxyoxan-2-yl]methyl acetate
  参考文献：
  名称：

  4-Methylumbelliferyl 2-acetamido-2-deoxy-α-d-glucopyranoside, a fluorogenic substrate for N-acetyl-α-D-glucos-aminidase

  摘要：

  Condensation of dimeric 3,4,6-tri-O-acetyl-2-deoxy-2-nitroso-alpha-D-glucopyranosyl chloride with 4-methylumbelliferone gave crystalline 4-methylumbelliferyl 3,4,6-tri-O-acetyl-2-deoxy-2-oximino-alpha-D-arabino-hexopyranoside. Acetylation of this adduct, reduction of the resulting crude O-acetyloxime with borane in oxolane, and acetylation gave the 3,4,6-tri-O-acetyl derivative of 4-methylumbelliferyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside (1). A new sensitive assay of N-acetyl-alpha-D-glucosaminidase (EC 3.2.1.50) is made possible by fluorometric measurement of 4-methylumbelliferone liberated by enzymic hydrolysis of glycoside 1. Such assays are illustrated by results obtained with enzyme preparations from pig liver and human-blood serum.

  DOI：

  10.1016/s0008-6215(00)84698-4

文献信息

• A novel method for the structural and configurational analysis of alkyl 3,4,6-tri-O-acetyl-2-deoxy-2-hydroxyimino-α-d-arabino- and-lyxo-hexopyranosides, using E.P.R. spectroscopy
  作者：Adri Mackor、Wolfgang A.R. van Heeswijk、Peter de Haan、Johannes F.G. Vliegenthart

  DOI：10.1016/s0008-6215(00)85204-0

  日期：1980.12

  corresponding Z- and E- isomeric iminoxy radicals ( > CNO), which gave very intense and persistent electron paramagnetic resonance (e.p.r.) signals. Applyina previous results for cyclohexane iminoxy radicals and the differences between the spectra of the arabino and lyxo compounds, it has been possible to assign the observed, hydrogen hyperfine structure for both Z - and E- radicals to the hexopyranoid-ring

  摘要用溶液中的乙酸铅（IV）氧化3,4,6-三-O-乙酰基-2-脱氧-2-羟基亚氨基-α-d-阿拉伯糖-和-lyxo-己吡喃糖苷烷基，生成相应的Z-和E-异构亚氨基氧基（> C = N = O），可产生非常强烈且持久的电子顺磁共振（epr）信号。应用先前关于环己烷亚氨基氧基的结果以及阿拉伯和lyxo化合物的光谱之间的差异，可以将观察到的Z-和E-氢超精细结构分配给C-处的六吡喃环氢原子1,3,4和5或6。从Z-和E-肟中，获得亚胺氧基的相同Z / E-平衡混合物。此外，根据溶剂和温度的影响，得出了有关六吡喃环结构的结论。
• Influence of the oxime and anomeric configurations on the stability of 2-deoxy-2-hydroxyimino- d -hexopyranosides
  作者：Magdalena Cyman、Justyna Wielińska、Henryk Myszka、Damian Trzybiński、Artur Sikorski、Andrzej Nowacki、Beata Liberek

  DOI：10.1016/j.molstruc.2016.07.019

  日期：2016.12

  Abstract The Z/E isomerisations of the synthesized benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-hydroxyimino- d -hexopyranosides during the NMR measurement and during the Zemplen O-deacetylation were observed. In order to study stabilities and tendency of the obtained compounds to isomerise, B3LYP/6-311++G∗∗ level geometry optimisations for four stereoisomers of methyl 2-deoxy-2-hydroxyimino- d -arabino-hexopyranosides

  摘要 合成的苄基 3,4,6-tri-O-acetyl-2-deoxy-2-hydroxyimino-d-hexopyranosides 在 NMR 测量期间和 Zemplen O-脱乙酰作用期间观察到 Z/E 异构化。为了研究所得化合物的稳定性和异构化趋势，B3LYP/6-311++G** 对甲基 2-脱氧-2-羟基亚氨基-d-阿拉伯-吡喃糖苷的四种立体异构体进行了几何优化。进行了乙酰化和 O-脱乙酰化形式。我们的理论研究结果与实验数据和核磁共振分析完全一致。此外，还报告了苄基 2-脱氧-2-羟基亚氨基-α-d-lyxo-hexopyranoside 的单晶 X 射线衍射数据，以补充我们的理论研究。
• Liberek; Frankowski; Smiatacz, Polish Journal of Chemistry, 1999, vol. 73, # 7, p. 1153 - 1161
  作者：Liberek、Frankowski、Smiatacz

  DOI：——

  日期：——
• US4063015A
  申请人：——

  公开号：US4063015A

  公开（公告）日：1977-12-13
• US4361701A
  申请人：——

  公开号：US4361701A

  公开（公告）日：1982-11-30