methyl (methyl 4-O-methyl-α-D-glucopyranosid)uronate | 31506-18-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (methyl 4-O-methyl-α-D-glucopyranosid)uronate
• 英文别名: Methyl uronate；Methyl(methyl 4-O-methyl-α-D-glucopyranosid)uronat；4-Methyl-β-D-methyl-glucuronosid-methylester；O¹,O⁴-dimethyl-α-D-glucopyranuronic acid methyl ester；O¹,O⁴-Dimethyl-α-D-glucopyranuronsaeure-methylester；Dimethyl 4-O-methylhexopyranosiduronate；methyl (2S,3S,4R,5R,6S)-4,5-dihydroxy-3,6-dimethoxyoxane-2-carboxylate
• CAS: 31506-18-0
• 化学式: C₉H₁₆O₇
• 分子量: 236.222
• InChiKey: VRQGSFPALWCJBE-RQYWWVFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (methyl 4-O-methyl-α-D-glucopyranosid)uronate 在 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 threo-1-<4-(benzyloxy)-3-methoxyphenyl>-3-chloroacetoxy-2-(2-methoxyphenoxy)propyl (methyl 4-O-methyl-α-D-glucopyranosid)uronate
  参考文献：
  名称：

  Synthesis and Rearrangement Reactions of Ester-Linked Lignin-Carbohydrate Model Compounds

  摘要：

  A series of ester-linked lignin-carbohydrate model compounds has been synthesized, which represent possible ester linkages of lignin to hemicellulose in wood through the carboxylic acid group of 4-O-methyl-alpha-D-glucopyranosiduronic acid moieties. The three and erythro isomers of these compounds were prepared through an appropriate combination of protective and stereoselective transformations. Spectroscopic characterization of these esters revealed that the uronosyl group migrated between the primary (gamma) and benzylic (alpha) positions of the lignin side chain in both acidic and neutral conditions. It has been determined that the migration equilibrium favors gamma- over alpha-esters, with the reaction possibly proceeding through a six-membered ring intermediate. That uronosyl migrations occur favoring the gamma-position suggests that the classical view of lignin-xylan ester linkages in wood needs to be reevaluated.

  DOI：

  10.1021/jf00056a026
• 作为产物：
  描述：

  methyl (methyl-2,3-bis-O-(phenylmethyl)-β-D-glucopyranoside)uronate 在 甲醇 、 钯 、 溶剂黄146 、 silver(l) oxide 作用下， 生成 methyl (methyl 4-O-methyl-α-D-glucopyranosid)uronate
  参考文献：
  名称：

  �ber 4-Methyl-glucurons�ure

  摘要：

  DOI：

  10.1007/bf00903021

文献信息

• Petrakova, Eva; Schraml, Jan; Hirsch, Jan, Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 6, p. 1501 - 1513
  作者：Petrakova, Eva、Schraml, Jan、Hirsch, Jan、Kvicalova, Magdalena、Zeleny, Jan、Chvalovsky, Vaclav

  DOI：——

  日期：——
• Synthesis of methyl ethers of methyl (methyl ?-D-glucopyranosid)uronate
  作者：E. V. Evtushenko、Yu. S. Ovodov

  DOI：10.1007/bf00602451

  日期：——
• Acetolysis of methyl (methyl 4-O-methyl-β-d-glucopyranosid)uronate
  作者：Osamu Kanie、Tadahiro Takeda、Yukio Ogihara

  DOI：10.1016/0008-6215(90)84153-l

  日期：1990.3
• Kovac; Brezny; Mihalov, Journal of Carbohydrates Nucleosides Nucleotides, 1975, vol. 2, # 6, p. 445 - 458
  作者：Kovac、Brezny、Mihalov、Palovcik

  DOI：——

  日期：——
• 588. The constitution of mesquite gum. Part III. The structure of the monomethyl glucuronic acid component
  作者：F. Smith

  DOI：10.1039/jr9510002646

  日期：——

表征谱图