phenyl 2,7-di-O-benzyl-4,6-O-benzylidene-D-glycero-1-thio-α-D-mannoheptopyranoside | 1060735-41-2

• 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: phenyl 2,7-di-O-benzyl-4,6-O-benzylidene-D-glycero-1-thio-α-D-mannoheptopyranoside
• CAS: 1060735-41-2
• 化学式: C₃₄H₃₄O₆S
• 分子量: 570.706
• InChiKey: JPDPGNWTWSEZNQ-QIOGARNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.15
• 重原子数：
  41.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  phenyl 2,7-di-O-benzyl-4,6-O-benzylidene-D-glycero-1-thio-α-D-mannoheptopyranoside 、 2-溴甲基萘 在 sodium hydride 、 四丁基碘化铵 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 12.83h， 以91%的产率得到phenyl 2,7-di-O-benzyl-4-O-benzylidene-3-O-(2-naphthalenylmethyl)-D-glycero-α-D-thio-manno-heptopyranoside
  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：

  (2R,3S,4S,5S,6R)-5-(benzyloxy)-2-((R)-2-(benzyloxy)-1-hydroxyethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4-diol 、 苯甲醛二甲缩醛 在 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以87%的产率得到phenyl 2,7-di-O-benzyl-4,6-O-benzylidene-D-glycero-1-thio-α-D-mannoheptopyranoside
  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