O¹-benzyl-β-D-glucopyranuronic acid methyl ester | 108852-23-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O¹-benzyl-β-D-glucopyranuronic acid methyl ester
• 英文别名: O¹-Benzyl-β-D-glucopyranuronsaeure-methylester；methyl (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-phenylmethoxyoxane-2-carboxylate
• CAS: 108852-23-9
• 化学式: C₁₄H₁₈O₇
• 分子量: 298.293
• InChiKey: ODHYLSMNMUSUIO-BYNIDDHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.82
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105.45
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  O¹-benzyl-β-D-glucopyranuronic acid methyl ester 在 palladium on activated charcoal 咪唑 、 4-二甲氨基吡啶 、 sodium hydroxide 、 偶氮二甲酸二异丙酯 、 氢气 、 氯磷酸二乙酯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 115.5h， 生成
  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：

  乙酰溴-Alpha-D-葡萄糖酮酸甲基酯 在 甲醇 、 4 A molecular sieve 、 sodium 、 silver carbonate 作用下， 以 苯 为溶剂， 反应 20.0h， 生成 O¹-benzyl-β-D-glucopyranuronic acid methyl ester
  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

• Conformational study of synthetic Δ4-uronate monosaccharides and glycosaminoglycan-derived disaccharides
  作者：Hélène G. Bazin、Ishan Capila、Robert J. Linhardt

  DOI：10.1016/s0008-6215(98)00118-9

  日期：1998.5

  carboxy group was protected as a methyl or benzyl ester, the anomeric hydroxyl group as a benzyl glycoside and the 2 and 3 hydroxyl groups were protected with different substitution patterns as both ester and ether derivatives. Disaccharides containing delta 4-uronates were prepared from heparin layses. Their carboxy group was unprotected or protected as a benzyl ester and the two hydroxyls in the uronate

  化学合成了十六种4-尿酸δ单糖。它们的羧基被保护为甲基或苄基酯，异头羟基被保护为苄基糖苷，而2和3个羟基分别被不同的取代方式保护为酯和醚衍生物。由肝素酶制备含4-尿酸δ的二糖。它们的羧基未被保护或被保护为苄基酯，并且在尿酸酯部分中的两个羟基是游离的，因为O-磺基衍生物或被酰化。通过检查质子间的邻位偶合常数，使用1 H NMR研究了这些不饱和尿酸盐单糖和二糖残基的构象。δ4-尿酸酯残基采用2H1或1H2构象。
• Helferich; Berger, Chemische Berichte, 1957, vol. 90, p. 2492,2495
  作者：Helferich、Berger

  DOI：——

  日期：——
• Regio and stereoselective conversion of Δ4-uronic acids to l-Ido- and d-glucopyranosiduronic acids
  作者：Hélène G Bazin、Robert.J Kerns、Robert J Linhardt

  DOI：10.1016/s0040-4039(96)02514-2

  日期：1997.2

  Synthesis of L-ido- and D-glucopyranosiduronic acids was performed starting from protected Delta(4)-uronic acids 3a-f. Bromination of the C-4,5 double bond provided the trans-diaxial bromohydrin derivatives 6a-d, which were converted to the corresponding epoxides 7a-d in high yields. Direct reduction of these epoxides using borane-tetrahydrofuran complex afforded the o-glucopyranosiduronic acids 9b-d, while Lewis acid rearrangment through the C-4 keto intermediate 10b-d afforded the L-idopyranosiduronic acids 11b-d. (C) 1997, Elsevier Science Ltd.