phenyl 2-O-benzyl-6,7-dideoxy-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-α-D-mannohepto-6-enopyranoside | 1060735-28-5

• 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-6,7-dideoxy-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-α-D-mannohepto-6-enopyranoside
• CAS: 1060735-28-5
• 化学式: C₂₆H₃₂O₆S
• 分子量: 472.602
• InChiKey: KMRDJAKZRXGKNJ-NYMVXWMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 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：
  0.46
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  phenyl 2-O-benzyl-6,7-dideoxy-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-α-D-mannohepto-6-enopyranoside 在 四氧化锇 、 (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan) 、 水 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 甲苯 、 叔丁醇 为溶剂， 反应 48.0h， 以68%的产率得到phenyl 2-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
• 作为产物：
  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