methyl 2,3,6-tri-O-benzyl-4-deoxy-4-C-formyl-α-D-mannopyranoside | 503456-79-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2,3,6-tri-O-benzyl-4-deoxy-4-C-formyl-α-D-mannopyranoside
• 英文别名: (2S,3R,4S,5S,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxane-3-carbaldehyde
• CAS: 503456-79-9
• 化学式: C₂₉H₃₂O₆
• 分子量: 476.569
• InChiKey: SPVINATXNPEEEO-PNHLWVRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3,6-tri-O-benzyl-4-deoxy-4-C-formyl-α-D-mannopyranoside 在 samarium diiodide 、 偶氮二异丁腈 、 五氟苯酚 、 三苯基氢化锡 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 3.17h， 生成 methyl 2,3,6-tri-O-benzyl-4-deoxy-4-C-[(2',3',4',6'-tetra-O-benzyl-α-D-mannopyranosyl)methyl]-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of the C-Linked Disaccharide α-d-Man-(1→4)-d-Man Employing a SmI₂-Mediated C-Glycosylation Step:  En Route to Cyclic C-Oligosaccharides

  摘要：

  Investigations are reported on the assembly of the C-linked disaccharide alpha-D-Man-(1-->4)-D-Man, representing the first steps in our projected synthesis of a cyclic C-oligomer containing repeating units of this C-dimer. The key step in this synthesis uses a SmI2-mediated coupling of 2,3,4,6-tetra-O-benzyl-alpha-D-mannopyranosyl 2'-pyridyl sulfone with a C4-formyl branched mannopyranoside unit, affording the C-disaccharide derivative with complete stereocontrol at the two new stereogenic centers. Subsequently, a modified tin hydride based deoxygenation produced the target carbohydrate analogue. The synthesis of the C4-formyl monosaccharide makes use of a stereoselective radical-based allylation followed by double bond migration and ozonolysis.

  DOI：

  10.1021/jo020585a
• 作为产物：
  描述：

  methyl 2,3,6-tri-O-benzoyl-α-D-mannopyranoside 在 rhodium(III) chloride 甲醇 、 过氧化双月桂酰 、 sodium methylate 、 sodium hydride 、 potassium carbonate 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 8.67h， 生成 methyl 2,3,6-tri-O-benzyl-4-deoxy-4-C-formyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of the C-Linked Disaccharide α-d-Man-(1→4)-d-Man Employing a SmI₂-Mediated C-Glycosylation Step:  En Route to Cyclic C-Oligosaccharides

  摘要：

  Investigations are reported on the assembly of the C-linked disaccharide alpha-D-Man-(1-->4)-D-Man, representing the first steps in our projected synthesis of a cyclic C-oligomer containing repeating units of this C-dimer. The key step in this synthesis uses a SmI2-mediated coupling of 2,3,4,6-tetra-O-benzyl-alpha-D-mannopyranosyl 2'-pyridyl sulfone with a C4-formyl branched mannopyranoside unit, affording the C-disaccharide derivative with complete stereocontrol at the two new stereogenic centers. Subsequently, a modified tin hydride based deoxygenation produced the target carbohydrate analogue. The synthesis of the C4-formyl monosaccharide makes use of a stereoselective radical-based allylation followed by double bond migration and ozonolysis.

  DOI：

  10.1021/jo020585a

文献信息

• Synthesis of the <i>C</i>-Linked Disaccharide α-<scp>d</scp>-Man-(1→4)-<scp>d</scp>-Man Employing a SmI₂-Mediated <i>C</i>-Glycosylation Step:  En Route to Cyclic <i>C</i>-Oligosaccharides
  作者：Lise Munch Mikkelsen、Troels Skrydstrup

  DOI：10.1021/jo020585a

  日期：2003.3.1

  Investigations are reported on the assembly of the C-linked disaccharide alpha-D-Man-(1-->4)-D-Man, representing the first steps in our projected synthesis of a cyclic C-oligomer containing repeating units of this C-dimer. The key step in this synthesis uses a SmI2-mediated coupling of 2,3,4,6-tetra-O-benzyl-alpha-D-mannopyranosyl 2'-pyridyl sulfone with a C4-formyl branched mannopyranoside unit, affording the C-disaccharide derivative with complete stereocontrol at the two new stereogenic centers. Subsequently, a modified tin hydride based deoxygenation produced the target carbohydrate analogue. The synthesis of the C4-formyl monosaccharide makes use of a stereoselective radical-based allylation followed by double bond migration and ozonolysis.