1,2,3,4-tetra-O-methyl-α-D-glucopyranuronic acid | 66657-20-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2,3,4-tetra-O-methyl-α-D-glucopyranuronic acid
• 英文别名: tetra-O-methyl-α-D-glucopyranuronic acid；Tetra-O-methyl-α-D-glucopyranuronsaeure；Methyl-2,3,4-tri-O-methyl-α-D-glucopyranosiduronic acid；2,3,4-Tri-O-methyl-D-glucuronsaeure-methyl-β-glucosid
• CAS: 66657-20-3
• 化学式: C₁₀H₁₈O₇
• 分子量: 250.249
• InChiKey: AOOJOHFWONACSA-OIOLOSQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.51
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetra-O-methyl-α-D-glucopyranuronic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成 1-methyl-3-((2R,3R,4S,5R,6S)-3,4,5,6-tetramethoxytetrahydro-2H-pyran-2-yl)quinoxalin-2(1H)-one
  参考文献：
  名称：

  可见光诱导通过脱羧 C-H 糖基化合成杂芳基 C-糖苷

  摘要：

  光氧化还原促进的脱羧 C-H 糖基化已被开发用于合成杂芳基C-糖苷。该方法的特点是反应体系极其简单、非对映选择性高、官能团耐受性好。此外，这种创新方法不需要高温、过渡金属和光催化剂，提供了一种环保、简单且高效的方案。

  DOI：

  10.1039/d4cc01328j
• 作为产物：
  描述：

  (2S,3R,4S,5R,6R)-2,3,4,5-tetramethoxy-6-((trityloxy)methyl)tetrahydro-2H-pyran 在 四丁基氟化铵 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 free radical 、 碳酸氢钠 作用下， 以 水 、 乙酸乙酯 为溶剂， 生成 1,2,3,4-tetra-O-methyl-α-D-glucopyranuronic acid
  参考文献：
  名称：

  Synthesis pathway to carbohydrate-derived salicylidene hydrazides as ligands for oxovanadium complexes

  摘要：

  Salicylidene hydrazides represent important ligands forming oxovanadium complexes. Carbohydrate-derived chiral salicylidene hydrazides as ligands for metal ion complexation were synthesized for the first time. The pathway of the mild and selective synthesis starts from commercial saccharides like methyl-alpha-D-glucopyranoside and methyl-alpha-D-mannopyranoside. All synthesized carbohydrate-derived salicylidene hydrazides are able to form oxovanadium complexes. The mononuclear structure proposed for the complex of 1,2,3,4-tetra-O-methyl-alpha-D-glucopyranuronic acid salicylidene hydrazide is consistent with the analytical data (NMR, IR and MS). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.094

文献信息

• Visible-light-mediated synthesis of non-anomericS-aryl glycosidesviaa photoactive electron-donor–acceptor complex
  作者：Le Zhang、Shiyun He、Jinyu Hou、Meiling Ye、Jian Chen、Guanghui Lv、Tianle Huang、Zhongzhen Yang、Yong Wu

  DOI：10.1039/d3cc03474g

  日期：——

  through which a series of S-aryl glycosides were obtained in good yields with satisfactory stereoselectivity. The preliminary mechanistic studies revealed that this transformation proceeded via an EDA complex. Moreover, the potential application value was demonstrated in the late-stage functionalisation of drug molecules and a gram-scale experiment.

  已报道了糖基氧化还原活性酯与二硫化物之间的可见光介导的糖基化反应，通过该反应以良好的收率和令人满意的立体选择性获得了一系列S-芳基糖苷。初步的机制研究表明，这种转变是通过EDA 复合体进行的。此外，潜在的应用价值在药物分子的后期功能化和克级实验中得到了证明。
• Conversion of Weinreb Amides into Benzene Rings Incorporating the Amide Carbonyl Carbon
  作者：Derrick L. J. Clive、Mai P. Pham

  DOI：10.1021/jo802629w

  日期：2009.2.20

  Esters, acids and acid chlorides can be converted via the intermediacy of their Corresponding Weinreb amides into benzene derivatives that incorporate the original carbonyl carbon as part of the benzene ring. The process involves treatment of the derived Weinreb amides with 3-butenylmagnesium bromide and an allylic Grignard reagent, followed by ring-closing metathesis, dehydration and dehydrogenation. The dehydration-dehydrogenation can be done under acidic conditions with a mixture of TsOH center dot H2O and DDQ or in two steps with SOCl2/Pyridine, followed by treatment with DDQ. Application of the method to carbohydrates provides a convenient route to C-5 aryl pyranosides.
• 353. The constitution of arabic acid. Part II. Degraded arabic acid
  作者：F. Smith

  DOI：10.1039/jr9390001724

  日期：——
• The Constitution of Mesquite Gum. I. The Methanolysis Products of Methylated Mesquite Gum^*
  作者：E. V. White

  DOI：10.1021/ja01206a037

  日期：1946.2