benzyl 2,3,4-tri-O-benzyl-β-D-glucopyranuronate | 125474-14-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,3,4-tri-O-benzyl-β-D-glucopyranuronate
• 英文别名: benzyl (2S,3S,4S,5R,6R)-6-hydroxy-3,4,5-tris(phenylmethoxy)oxane-2-carboxylate
• CAS: 125474-14-8
• 化学式: C₃₄H₃₄O₇
• 分子量: 554.64
• InChiKey: JGZVCCVFRMQHQJ-DUDMTIKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,2,3,4-四-O-乙酰基-Β-D-葡萄糖醛酸甲酯 在 N-碘代丁二酰亚胺 、 三氟化硼乙醚 、 水 、 sodium methylate 、 silver trifluoromethanesulfonate 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 15.25h， 生成 benzyl 2,3,4-tri-O-benzyl-β-D-glucopyranuronate
  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

文献信息

• Synthesis of Bile Acid 24-acyl Glucuronides
  作者：Junichi Goto、Naoaki Murao、Junji Oohashi、Shigeo Ikegawa

  DOI：10.1016/s0039-128x(97)00160-8

  日期：1998.4

  The synthesis of acyl glucuronides of common bile acids is described By means of the Mitsunobu reaction employing diethylazodicarboxylate and triphenylphosphine, bile acids were condensed through the inherent C-24 carboxy group with benzyl,2,3,4-tri-O-benzyl-D-glucopyranuronate which was prepared from 1-O-methyl-alpha-D-glucose, The separation and purification of the beta-anomers at the anomeric position of the sugar moiety were attained by preparative thin-layer chromatography and/or high-performance liquid chromatography on a column packed with phenyl-bonded silica using H2O-MeOH as a mobile phase. The removal of the benzyl group on the sugar moiety was achieved by catalytic hydrogenation,with 10% palladium on carbon to yield the desired acyl glucuronides of bile acids. The structures of these acyl glucuronides were confirmed by proton nuclear magnetic resonance spectral properties. (C) 1998 by Elsevier Science Inc.
• 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.