methyl 3,4-di-O-benzyl-β-L-rhamnopyranoside | 111723-27-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4-di-O-benzyl-β-L-rhamnopyranoside
• 英文别名: (2S,3R,4S,5S,6S)-2-methoxy-6-methyl-4,5-bis(phenylmethoxy)oxan-3-ol
• CAS: 111723-27-4
• 化学式: C₂₁H₂₆O₅
• 分子量: 358.434
• InChiKey: TVXGZVODGVJJEY-YSCIFQABSA-N

物化性质

• 沸点：
  491.0±45.0 °C(predicted)
• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3,4-di-O-benzyl-β-L-rhamnopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 72.0h， 生成 (2S,3R,4R,5R,6S)-2-Methoxy-6-methyl-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  Kamiya, Shintaro; Esaki, Sachiko; Shiba, Naoko, Agricultural and Biological Chemistry, 1987, vol. 51, p. 2207 - 2214

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-α-L-quinoxopyranose 在 sodium tetrahydroborate 、 sodium methylate 、 乙酸酐 、 四氯化锡 、 二甲基亚砜 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 51.0h， 生成 methyl 3,4-di-O-benzyl-β-L-rhamnopyranoside
  参考文献：
  名称：

  Kamiya, Shintaro; Esaki, Sachiko; Shiba, Naoko, Agricultural and Biological Chemistry, 1987, vol. 51, p. 2207 - 2214

  摘要：

  DOI：

文献信息

• Allyl protecting group mediated intramolecular aglycon delivery (IAD): synthesis of α-glucofuranosides and β-rhamnopyranosides
  作者：Ian Cumpstey、Antony J. Fairbanks、Alison J. Redgrave

  DOI：10.1016/j.tet.2004.07.083

  日期：2004.10

  The use of allyl protecting group mediated intramolecular aglycon delivery (IAD) as a strategy for intramolecular glycosylation has been extended to allow the stereoselective synthesis of α-glucofuranosides and β-rhamnopyranosides, in a totally stereoselective fashion. The efficiency of intramolecular glycosylation is dependent on the protecting group pattern of the glycosyl donor, and on the steric

  使用烯丙基保护基介导的分子内糖苷配基（IAD）作为分子内糖基化的策略已得到扩展，以完全立体选择性的方式允许α-葡糖呋喃糖苷和β-鼠李糖吡喃糖苷的立体选择性合成。分子内糖基化的效率取决于糖基供体的保护基团模式以及糖基受体的空间体积。
• Kamiya, Shintaro; Esaki, Sachiko; Tanaka, Reiko, Agricultural and Biological Chemistry, 1985, vol. 49, # 1, p. 55 - 62
  作者：Kamiya, Shintaro、Esaki, Sachiko、Tanaka, Reiko

  DOI：——

  日期：——
• Chemistry of 1-Alkoxy-1-glycosyl Radicals:  The Manno- and Rhamnopyranosyl Series. Inversion of α- to β-Pyranosides and the Fragmentation of Anomeric Radicals
  作者：David Crich、Sanxing Sun、Jarmila Brunckova

  DOI：10.1021/jo951194h

  日期：1996.1.1

  The formation and stereoselective quenching of 1-mannopyranosyl radicals by a tributyltin hydride-mediated intramolecular 1,5-hydrogen abstraction sequence is described. A competing process is 1,4-hydrogen atom abstraction leading principally to glucopyran-2-ulosides. Fragmentation of the anomeric radical resulting in the formation of ring opened products is a problem in certain series. The chemistry is dictated to a considerable extent by the nature of the protecting groups employed with the 4,6-benzylidene series and, for rhamnose, the Ley 3,4-dispiroketal, being particularly susceptible to the 1,4-hydrogen atom abstraction but less to the fragmentation. Photochemical conditions are described, in which these side reactions are practically eliminated, and applied to the inversion of an alpha- to a beta-mannoside in a disaccharide.
• KAMIYA, SHINTARO;ESAKI, SACHIKO;SHIBA, NAOKO, AGR. AND BIOL. CHEM., 51,(1987) N 8, 2207-2214
  作者：KAMIYA, SHINTARO、ESAKI, SACHIKO、SHIBA, NAOKO

  DOI：——

  日期：——