Isopropyl-2,3,4-tri-O-acetyl-β-D-glucopyranosid-uronsaeure-methylester | 92420-83-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Isopropyl-2,3,4-tri-O-acetyl-β-D-glucopyranosid-uronsaeure-methylester
• 英文别名: O²,O³,O⁴-Triacetyl-O¹-isopropyl-β-D-glucopyranuronsaeure-methylester；methyl (i-propyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate；methyl (2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-propan-2-yloxyoxane-2-carboxylate
• CAS: 92420-83-2
• 化学式: C₁₆H₂₄O₁₀
• 分子量: 376.361
• InChiKey: WMLVFLHCFASTLY-GRYWWWGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Isopropyl-2,3,4-tri-O-acetyl-β-D-glucopyranosid-uronsaeure-methylester 生成 (4S,5R,6R)-4,5-Diacetoxy-6-isopropoxy-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Rapid access to uronic acid-based mimetics of Kdn2en from d-glucurono-6,3-lactone

  摘要：

  A concise route to novel mimetics of Kdn2en, based on Delta(4)-uronic acids, from D-glucurono-6,3-lactone is presented. Uronic acid-based mimetics in which an aliphatic ether (O-glycoside), a thioether (S-glycoside), or acetamide takes the place of the natural C-6 glycerol sidechain of the sialic acid were synthesized from the key intermediate, methyl 2,3,4-tri-O-acetyl-alpha-D-glucopyranosyluronate bromide. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00228-7
• 作为产物：
  描述：

  D-GLUCURONIDEMETHYLESTERD-葡糖苷酸甲酯 在 silver carbonate 高氯酸 、 3 A molecular sieve 、 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 生成 Isopropyl-2,3,4-tri-O-acetyl-β-D-glucopyranosid-uronsaeure-methylester
  参考文献：
  名称：

  Rapid access to uronic acid-based mimetics of Kdn2en from d-glucurono-6,3-lactone

  摘要：

  A concise route to novel mimetics of Kdn2en, based on Delta(4)-uronic acids, from D-glucurono-6,3-lactone is presented. Uronic acid-based mimetics in which an aliphatic ether (O-glycoside), a thioether (S-glycoside), or acetamide takes the place of the natural C-6 glycerol sidechain of the sialic acid were synthesized from the key intermediate, methyl 2,3,4-tri-O-acetyl-alpha-D-glucopyranosyluronate bromide. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00228-7

文献信息

• Koenigs–Knorr reaction of fusel alcohols with methyl (1-bromo-2,3,4-tri-O-acetyl-α-d-glucopyranosid)uronate leading to the protected alkyl glucuronides—crystal structures and high resolution 1H and 13C NMR data
  作者：Bettina Mönch、Antje Gebert、Franziska Emmerling、Roland Becker、Irene Nehls

  DOI：10.1016/j.carres.2012.01.002

  日期：2012.5

  Crystal structures and high resolution (1)H and (13)C NMR spectral data for methyl (alkyl 2,3,4-tri-O-acetyl-beta-D-glucopyranosid)uronates (alkyl=methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, i-butyl, n-pentyl, 2-methyl-1-butyl and 3-methyl-1-butyl) are presented.

  甲基（烷基2,3,4-三-O-乙酰基-β-D-吡喃葡萄糖苷）尿酸（烷基=甲基，乙基，正丙基）的晶体结构和高分辨率（1）H和（13）C NMR光谱数据给出了异丙基，正丁基，仲丁基，异丁基，正戊基，2-甲基-1-丁基和3-甲基-1-丁基。
• A novel method for stereoselective glucuronidation
  作者：Bilha Fischer、Abraham Nudelman、Margareta Ruse、Jacob Herzig、Hugo E. Gottlieb、Ehud Keinan

  DOI：10.1021/jo00199a046

  日期：1984.12
• Sasaki, Yasuhiro; Morita, Toshinobu; Kuramoto, Takashi, Agricultural and Biological Chemistry, 1988, vol. 52, # 1, p. 207 - 210
  作者：Sasaki, Yasuhiro、Morita, Toshinobu、Kuramoto, Takashi、Mizutani, Kenji、Ikeda, Ryuko、Tanaka, Osamu

  DOI：——

  日期：——