methyl 2,3,5-tri-O-methyl-D-ribofuranoside | 14520-04-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,5-tri-O-methyl-D-ribofuranoside
• 英文别名: (2S,3R,4R,5R)-2,3,4-trimethoxy-5-(methoxymethyl)oxolane
• CAS: 14520-04-8
• 化学式: C₉H₁₈O₅
• 分子量: 206.239
• InChiKey: GGXQVNLZJSOZBN-BGZDPUMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2,3,5-tri-O-methyl-D-ribofuranoside 在 dimethyl sulfide borane 、 丁基三氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 1,4-anhydro-D-ribitol
  参考文献：
  名称：

  Reductive cleavage of permethylated polysaccharides with borane-methyl sulfide complex and butyltin trichloride

  摘要：

  Several per-O-methylated monosaccharides and polysaccharides were used as models in an attempt to identify more convenient reagents for accomplishing reductive cleavage of glycosidic linkages. Included in the model studies were methyl alpha- and beta-D-glucopyranoside, methyl alpha- and beta-D-mannopyranoside, and methyl alpha- and beta-D-ribofuranoside. These studies led to the identification of a new promoter, butyltin trichloride, for carrying out reductive cleavage when borane-methyl sulfide complex was used as the reducing agent. These reagents were found to accomplish the reductive cleavage of per-O-methylated amylose, cellulose, and pullulan to give only the expected derivatives of 1,5-anhydro-D-glucitol. These reagents also accomplished reductive cleavage of per-O-methylated inulin to give only the expected derivatives of 2,5-anhydro-D-mannitol and 2,5-anhydro-D-glucitol. Reductive cleavage using these reagents is easy to perform, and subsequent acetylation of the products is readily accomplished in situ. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00312-6
• 作为产物：
  描述：

  α,β-1-甲基-D-呋喃核糖苷 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.08h， 生成 methyl 2,3,5-tri-O-methyl-β-D-ribofuranoside 、 methyl 2,3,5-tri-O-methyl-D-ribofuranoside
  参考文献：
  名称：

  阳极偶联反应与C-糖苷的合成

  摘要：

  已经开发了一种方便的两步程序，用于将糖衍生物转化为含有被掩盖的醛官能团的C-糖苷。该化学方法利用了富电子烯烃与醇之间的阳极偶联反应。如果使用极化度较低的乙烯基硫醚衍生的自由基阳离子中间体，则该序列可同时形成呋喃糖和吡喃糖衍生物。使用更多极化的烯醇醚衍生的自由基阳离子，环化最适合形成呋喃糖衍生物，其中五元环的形成速率阻止了自由基阳离子引发的消除反应。

  DOI：

  10.1021/ol100800u

文献信息

• Anodic Coupling Reactions and the Synthesis of C-Glycosides
  作者：Guoxi Xu、Kevin D. Moeller

  DOI：10.1021/ol100800u

  日期：2010.6.4

  convenient, two-step procedure has been developed for converting sugar derivatives into C-glycosides containing a masked aldehyde functional group. The chemistry takes advantage of an anodic coupling reaction between an electron-rich olefin and an alcohol. The sequence works for the formation of both furanose and pyranose derivatives if less polarized vinyl sulfide derived radical cation intermediates are

  已经开发了一种方便的两步程序，用于将糖衍生物转化为含有被掩盖的醛官能团的C-糖苷。该化学方法利用了富电子烯烃与醇之间的阳极偶联反应。如果使用极化度较低的乙烯基硫醚衍生的自由基阳离子中间体，则该序列可同时形成呋喃糖和吡喃糖衍生物。使用更多极化的烯醇醚衍生的自由基阳离子，环化最适合形成呋喃糖衍生物，其中五元环的形成速率阻止了自由基阳离子引发的消除反应。
• Reductive cleavage of permethylated polysaccharides with borane-methyl sulfide complex and butyltin trichloride
  作者：Nan Wang、Gary R. Gray

  DOI：10.1016/s0008-6215(96)00312-6

  日期：1997.3

  Several per-O-methylated monosaccharides and polysaccharides were used as models in an attempt to identify more convenient reagents for accomplishing reductive cleavage of glycosidic linkages. Included in the model studies were methyl alpha- and beta-D-glucopyranoside, methyl alpha- and beta-D-mannopyranoside, and methyl alpha- and beta-D-ribofuranoside. These studies led to the identification of a new promoter, butyltin trichloride, for carrying out reductive cleavage when borane-methyl sulfide complex was used as the reducing agent. These reagents were found to accomplish the reductive cleavage of per-O-methylated amylose, cellulose, and pullulan to give only the expected derivatives of 1,5-anhydro-D-glucitol. These reagents also accomplished reductive cleavage of per-O-methylated inulin to give only the expected derivatives of 2,5-anhydro-D-mannitol and 2,5-anhydro-D-glucitol. Reductive cleavage using these reagents is easy to perform, and subsequent acetylation of the products is readily accomplished in situ. (C) 1997 Elsevier Science Ltd.