phenyl 2-O-benzyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-α-D-mannopyranoside | 1060735-24-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-O-benzyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-α-D-mannopyranoside
• CAS: 1060735-24-1
• 化学式: C₂₅H₃₂O₇S
• 分子量: 476.591
• InChiKey: FBTHSZMHROIVTK-MVKKGCRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  75.61
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  phenyl 2-O-benzyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-α-D-mannopyranoside 、 二甲基亚砜 、 亚甲基三苯基膦烷 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 四氢呋喃 、 hexanede 为溶剂， 反应 8.5h， 以84%的产率得到phenyl 2-O-benzyl-6,7-dideoxy-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-α-D-mannohepto-6-enopyranoside
  参考文献：
  名称：

  Block Synthesis of Tetra- and Hexasaccharides (β-d-Glycero-d-manno-Hepp-(1→4)-[α-l-Rhap-(1→3)-β-d-glycero-d-manno-Hepp-(1→4)]_n-α-l-Rhap-OMe (n = 1 and 2)) Corresponding to Multiple Repeat Units of the Glycan from the Surface-Layer Glycoprotein from Bacillus thermoaerophilus

  摘要：

  A fully stereocontrolled block synthesis of the title tetra- and hexasaccharides has been achieved taking advantage of the ability of the 4,6-O-benzylidene acetal to control the stereochemistry of the beta-D-glycero-D-mannoheptopyranoside unit and of a 2,3-O-diphenylmethylene acetal to install the alpha-L-rhamnopyranosidic linkages. Comparison of the spectral data for the hexasaccharide with that of the natural isolate confirms the structure of this very unusual and structurally challenging glycan.

  DOI：

  10.1021/jo801414c
• 作为产物：
  描述：

  溴甲苯 、 phenyl 3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-1-thio-α-D-mannopyranoside 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 17.0h， 以81%的产率得到phenyl 2-O-benzyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Block Synthesis of Tetra- and Hexasaccharides (β-d-Glycero-d-manno-Hepp-(1→4)-[α-l-Rhap-(1→3)-β-d-glycero-d-manno-Hepp-(1→4)]_n-α-l-Rhap-OMe (n = 1 and 2)) Corresponding to Multiple Repeat Units of the Glycan from the Surface-Layer Glycoprotein from Bacillus thermoaerophilus

  摘要：

  A fully stereocontrolled block synthesis of the title tetra- and hexasaccharides has been achieved taking advantage of the ability of the 4,6-O-benzylidene acetal to control the stereochemistry of the beta-D-glycero-D-mannoheptopyranoside unit and of a 2,3-O-diphenylmethylene acetal to install the alpha-L-rhamnopyranosidic linkages. Comparison of the spectral data for the hexasaccharide with that of the natural isolate confirms the structure of this very unusual and structurally challenging glycan.

  DOI：

  10.1021/jo801414c