phenyl 2,7-di-O-benzyl-4,6-O-benzylindene-3-O-(2-naphthalenylmethyl)-D-glycero-β-D-mannoheptopyranosyl-(1-4)-2,3-O-(diphenylmethylene)-1-thio-α-L-rhamnopyranoside | 1060735-52-5

• 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-4,6-O-benzylindene-3-O-(2-naphthalenylmethyl)-D-glycero-β-D-mannoheptopyranosyl-(1-4)-2,3-O-(diphenylmethylene)-1-thio-α-L-rhamnopyranoside
• CAS: 1060735-52-5
• 化学式: C₆₄H₆₀O₁₀S
• 分子量: 1021.24
• InChiKey: BRFCAHSZXIBGHM-SFENDCKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.34
• 重原子数：
  75.0
• 可旋转键数：
  17.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  92.3
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl 2,7-di-O-benzyl-4,6-O-benzylindene-D-glycero-β-D-mannoheptopyranosyl-(1-4)-2,3-O-(diphenylmethylene)-α-L-rhamnopyranoside 、 phenyl 2,7-di-O-benzyl-4,6-O-benzylindene-3-O-(2-naphthalenylmethyl)-D-glycero-β-D-mannoheptopyranosyl-(1-4)-2,3-O-(diphenylmethylene)-1-thio-α-L-rhamnopyranoside 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以85%的产率得到methyl 2,7-di-O-benzyl-4,6-O-benzylindene-3-O-(2-naphthaleneylmethyl)-D-glycero-β-D-mannoheptopyranosyl-(1-4)-2,3-O-(diphenylmethylene)-α-L-rhamnopyranosyl-(1-3)-2,7-di-O-benzyl-4,6-O-benzylindene-D-glycero-β-D-mannoheptopyranosyl-(1-4)-2,3-O-(diphenylmethylene)-α-L-rhamnopyranoside
  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 2,7-di-O-benzyl-4-O-benzylidene-3-O-(2-naphthalenylmethyl)-D-glycero-α-D-thio-manno-heptopyranoside 、 phenyl 2,3-O-(diphenylmethylene)-1-thio-α-L-rhamnopyranoside 在 1-(苯基亚硫酰基)哌啶 、 2,4,6-三叔丁基吡啶 、 辛烯 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 1.08h， 以73%的产率得到phenyl 2,7-di-O-benzyl-4,6-O-benzylindene-3-O-(2-naphthalenylmethyl)-D-glycero-β-D-mannoheptopyranosyl-(1-4)-2,3-O-(diphenylmethylene)-1-thio-α-L-rhamnopyranoside
  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