phenyl 2,7-di-O-benzyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-D-glycero-1-thio-α-D-mannoheptopyranoside | 1060735-39-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,7-di-O-benzyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-D-glycero-1-thio-α-D-mannoheptopyranoside
• 英文别名: (1R)-1-[(2S,3S,4aS,5R,7R,8S,8aS)-2,3-dimethoxy-2,3-dimethyl-8-phenylmethoxy-7-phenylsulfanyl-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxin-5-yl]-2-phenylmethoxyethanol
• CAS: 1060735-39-8
• 化学式: C₃₃H₄₀O₈S
• 分子量: 596.742
• InChiKey: MCHKUDFYYNNJPF-SJGYSAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  42
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  phenyl 2,7-di-O-benzyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-D-glycero-1-thio-α-D-mannoheptopyranoside 在 水 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以89%的产率得到(2R,3S,4S,5S,6R)-5-(benzyloxy)-2-((R)-2-(benzyloxy)-1-hydroxyethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4-diol
  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：

  在 水 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以331 mg的产率得到phenyl 2,7-di-O-benzyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-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