2,2,2-trichloroethyl 2,3,4-tri-O-tert-butyldimethylsilyl-D-glucopyranuronate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,2-trichloroethyl 2,3,4-tri-O-tert-butyldimethylsilyl-D-glucopyranuronate
• 英文别名: 2,2,2-trichloroethyl (2S,3R,4S,5R)-3,4,5-tris[[tert-butyl(dimethyl)silyl]oxy]-6-hydroxyoxane-2-carboxylate
• 化学式: C₂₆H₅₃Cl₃O₇Si₃
• 分子量: 668.318
• InChiKey: OAHKCLMDCMZOEH-FTXGJLNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.79
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,2,2-trichloroethyl 2,3,4-tri-O-tert-butyldimethylsilyl-D-glucopyranuronate 在 KH₂PO₄ buffer 、 偶氮二甲酸二异丙酯 、 三苯基膦 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 (2S,3R,4S,5R)-3,4,5-Tris-(tert-butyl-dimethyl-silanyloxy)-6-{2-[2-(4-chloro-phenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl]-acetoxy}-tetrahydro-pyran-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological identification of the acyl glucuronide of the antiinflammatory drug ML-3000

  摘要：

  The synthesis and identification in biological samples of the 1-O-acyl glucuronide 6 of the antiinflammatory drug ML-3000 is described. Starting with D-glucuronic acid gamma-lactone, 2,3,4-tris(tert.-butyldimethysilyl) glucuronic acid trichloroethylester 4 was prepared (in seven steps) and subsequently coupled with 1 under Mitsunobu conditions. Deprotection, i. e. removal of the trichloroethoxy group with zinc dust and desilylation with hydrofluoric acid in acetonitrile afforded a mixture of alpha- and beta-6 which could be separated by preparative HPLC. The abundance of 6 in bile and plasma samples obtained from animal studies with the cynomolgus monkey and the rabbit following repeated administration of 1 could be demonstrated by LC-electrospray MS analysis. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00123-6
• 作为产物：
  描述：

  苄基beta-D-吡喃葡糖苷酸甲酯三乙酸酯 在 palladium on activated charcoal 咪唑 、 甲醇 、 4-二甲氨基吡啶 、 sodium hydroxide 、 氢气 、 sodium 、 氯磷酸二乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， -40.0~80.0 ℃ 、101.33 kPa 条件下， 反应 82.0h， 生成 2,2,2-trichloroethyl 2,3,4-tri-O-tert-butyldimethylsilyl-D-glucopyranuronate
  参考文献：
  名称：

  α，β-不饱和羧酸的葡糖苷酸的合成

  摘要：

  摘要描述了一种实用的α，β-不饱和羧酸葡萄糖醛酸合成方法。该方法的要点是使用在非还原条件下可除去的基团来保护葡萄糖醛酸。

  DOI：

  10.1016/0008-6215(93)80097-x

文献信息

• Synthesis of glucuronides of α,β-unsaturated carboxylic acids
  作者：Masayuki Tanaka、Makoto Okita、Isao Yamatsu

  DOI：10.1016/0008-6215(93)80097-x

  日期：1993.3

  Abstract A practical synthetic method for glucuronides of α,β-unsaturated carboxylic acids is described. An essential point of this method is the use of groups removable using non-reducing conditions for the protection of the glucuronic acid.

  摘要描述了一种实用的α，β-不饱和羧酸葡萄糖醛酸合成方法。该方法的要点是使用在非还原条件下可除去的基团来保护葡萄糖醛酸。
• Synthesis and biological identification of the acyl glucuronide of the antiinflammatory drug ML-3000
  作者：Andreas Kirschning、Monika Ries、Silvie Domann、Wolfgang Martin、Wolfgang Albrecht、Peter Arnold、Stefan Laufer

  DOI：10.1016/s0960-894x(97)00123-6

  日期：1997.1

  The synthesis and identification in biological samples of the 1-O-acyl glucuronide 6 of the antiinflammatory drug ML-3000 is described. Starting with D-glucuronic acid gamma-lactone, 2,3,4-tris(tert.-butyldimethysilyl) glucuronic acid trichloroethylester 4 was prepared (in seven steps) and subsequently coupled with 1 under Mitsunobu conditions. Deprotection, i. e. removal of the trichloroethoxy group with zinc dust and desilylation with hydrofluoric acid in acetonitrile afforded a mixture of alpha- and beta-6 which could be separated by preparative HPLC. The abundance of 6 in bile and plasma samples obtained from animal studies with the cynomolgus monkey and the rabbit following repeated administration of 1 could be demonstrated by LC-electrospray MS analysis. (C) 1997 Elsevier Science Ltd.