benzyl <1-O-trichloroethanimidoyl>-2,3,4-tri-O-benzyl-D-glucopyranuronate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl <1-O-trichloroethanimidoyl>-2,3,4-tri-O-benzyl-D-glucopyranuronate
• 英文别名: benzyl 1-O-trichloroacetimidoyl-2,3,4-tri-O-benzyl-D-glucopyranuronate；Benzyl (2S,3S,4S,5R)-3,4,5-tris(benzyloxy)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-2-carboxylate；benzyl (2S,3S,4S,5R)-3,4,5-tris(phenylmethoxy)-6-(2,2,2-trichloroethanimidoyl)oxyoxane-2-carboxylate
• 化学式: C₃₆H₃₄Cl₃NO₇
• 分子量: 699.027
• InChiKey: BPINMQTUNMBWAP-UQZXYJODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  47
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  96.3
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl <1-O-trichloroethanimidoyl>-2,3,4-tri-O-benzyl-D-glucopyranuronate 在 palladium on activated charcoal 三氟化硼乙醚 、 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， -30.0~20.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 生成 萘普生葡糖苷酸
  参考文献：
  名称：

  Synthesis of Urine Drug Metabolites: Glucuronosyl Esters of Carboxymefloquine, Indoprofen, (S)‐Naproxen, and Desmethyl (S)‐Naproxen

  摘要：

  A general procedure for the synthesis of 1-O-acyl-beta-D-glucuronic acids using the benzyl 1-O-trichloroacetimidoyl-2,3,4-tri-O-benzyl-D-glucopyranuronate 6 as donor is exemplified by the synthesis of the urine metabolites of (S)-naproxen, desmethyl (S)-naproxen, indoprofen, and carboxymefloquine. The key intermediate benzyl 2,3,4-tri-O-benzyl-D-glucopyranuronate 5 is easily accessible in four steps (29%) from the peracetylated beta-D-glucuronic acid 1.

  DOI：

  10.1081/car-120034003
• 作为产物：
  描述：

  在 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 17.0h， 生成 benzyl <1-O-trichloroethanimidoyl>-2,3,4-tri-O-benzyl-D-glucopyranuronate
  参考文献：
  名称：

  卡芬太尼双相代谢物的合成

  摘要：

  卡芬太尼是一种超强效合成阿片类药物。俄罗斯警察部队使用卡芬太尼和瑞芬太尼解决了莫斯科的人质事件。这一报道的用途引发了人们对卡芬太尼在人体内的药理学和毒理学的兴趣，随后公布了其代谢物的数据。但目前对卡芬太尼代谢物合成的研究较少，生物提取也给后续研究提出了较大的不确定性。本研究的目的是研究卡芬太尼独特的双相代谢物的合成。目的是方便、快速、低成本地生产相应的代谢物，用于与已发表的结构进行比较，并证实卡芬太尼的给药效果。

  DOI：

  10.3390/molecules28227625

文献信息

• Identification of the Positional Isomers of 2-Fluorobenzoic acid 1-O-Acyl Glucuronide by Directly Coupled HPLC-NMR
  作者：Ulla G. Sidelmann、Claire. Gavaghan、Howard A. J. Carless、R. Duncan. Farrant、John C. Lindon、Ian D. Wilson、Jeremy K. Nicholson

  DOI：10.1021/ac00115a006

  日期：1995.10.1

  Directly coupled HPLC-IH NMR was used in the ''stop-flow'' mode to separate and rapidly identify an equilibrated mixture of ester glucuronide isomers formed spontaneously by intramolecular rearrangement reactions (internal acyl migration and mutarotation) of 2-fluorobenzoic acid beta-1-glucuronide (1-O-(2-fluorobenzoyl)-D-glucopyranuronic acid). The equilibrated mixture of isomers was obtained by incubation of the synthetic 2-fluorobenzoic acid glucuronide in buffer solution (pH 7.4) at 25 degrees C for 24 h. The beta-anomer of the 1-O-acyl glucuronide, and the 2-, 3-, and 4-positional glucuronide isomers (all three as both alpha- and beta-anomers) present in the equilibrium mixture, were all characterized after separation in an isocratic chromatographic system containing phosphate buffer at pH 7.4 and 1% acetonitrile in the mobile phase. The HPLC-NMR investigations also elucidated the mutarotation of the positional glucuronide isomers as well as showing the benefits of the HPLC-NMR technique as a primary analytical tool. This HPLC-NMR method will be of particular value in studies on the acyl migration reactions of nonsteroidal antiinflammatory drug glucuronides which may be related to their toxicological properties.
• Synthesis of Urine Drug Metabolites: Glucuronosyl Esters of Carboxymefloquine, Indoprofen, (<i>S</i>)‐Naproxen, and Desmethyl (<i>S</i>)‐Naproxen
  作者：Martina Lahmann、Moa Andresen Bergström、Dominika Turek、Stefan Oscarson

  DOI：10.1081/car-120034003

  日期：2004.12.26

  A general procedure for the synthesis of 1-O-acyl-beta-D-glucuronic acids using the benzyl 1-O-trichloroacetimidoyl-2,3,4-tri-O-benzyl-D-glucopyranuronate 6 as donor is exemplified by the synthesis of the urine metabolites of (S)-naproxen, desmethyl (S)-naproxen, indoprofen, and carboxymefloquine. The key intermediate benzyl 2,3,4-tri-O-benzyl-D-glucopyranuronate 5 is easily accessible in four steps (29%) from the peracetylated beta-D-glucuronic acid 1.
• The Synthesis of Biphasic Metabolites of Carfentanil
  作者：Junchang Wang、Jianwen Hu、Pingyong Liao、Shang Xue、Shan He、Ruijia Chen、Xuejun Zhao、Wenbin Liu

  DOI：10.3390/molecules28227625

  日期：——

  and data on its metabolites were later published. However, there have been few studies on the synthesis of carfentanil metabolites, and biological extraction has also put forward large uncertainty in subsequent studies. The aim of the present study is to investigate the synthesis of biphasic metabolites that are unique to carfentanil. The purpose was to produce corresponding metabolites conveniently,

  卡芬太尼是一种超强效合成阿片类药物。俄罗斯警察部队使用卡芬太尼和瑞芬太尼解决了莫斯科的人质事件。这一报道的用途引发了人们对卡芬太尼在人体内的药理学和毒理学的兴趣，随后公布了其代谢物的数据。但目前对卡芬太尼代谢物合成的研究较少，生物提取也给后续研究提出了较大的不确定性。本研究的目的是研究卡芬太尼独特的双相代谢物的合成。目的是方便、快速、低成本地生产相应的代谢物，用于与已发表的结构进行比较，并证实卡芬太尼的给药效果。