p-methoxyphenyl-2,3,6-tri-O-benzyl-4-propargyl-α-D-mannopyranoside | 674777-76-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl-2,3,6-tri-O-benzyl-4-propargyl-α-D-mannopyranoside
• 英文别名: Bn(-2)[Bn(-3)][prop-2-ynyl(-4)][Bn(-6)]Man(a)-O-Ph(4-OMe)；(2R,3S,4S,5R,6R)-2-(4-methoxyphenoxy)-3,4-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-5-prop-2-ynoxyoxane
• CAS: 674777-76-5
• 化学式: C₃₇H₃₈O₇
• 分子量: 594.705
• InChiKey: UZLDETOJFCFLPE-DWCHZDDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  44
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl-2,3,6-tri-O-benzyl-4-propargyl-α-D-mannopyranoside 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.25h， 生成 2,3,6-tri-O-benzyl-4-propargyl-β-D-mannopyranoside 、 2,3,6-tri-O-benzyl-4-propargyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of Readily Modifiable Cyclodextrin Analogues via Cyclodimerization of an Alkynyl−Azido Trisaccharide

  摘要：

  A convergent strategy for the synthesis of beta-cyclodextrin analogues is reported, utilizing preferential cyclodimerization of an azido-alkyne trisaccharide via Cu(I)-catalyzed [3 + 2] dipolar cycloaddition of the alkyne and azide functional groups. The resultant oligosaccharide macrocycle retains the binding propensity of cyclodextrins, as demonstrated by the similar ANS association constants measured for macrocycle 1 and beta-cyclodextrin. This new synthetic strategy opens up new avenues for modular preparation of functionally diverse cyclodextrin analogues that are otherwise inaccessible.

  DOI：

  10.1021/ja039374t
• 作为产物：
  描述：

  p-methoxyphenyl-4,6-O-benzylidene-2,3-O-benzyl-α-D-mannopyranoside 在 三乙基硅烷 、 sodium hydride 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.17h， 生成 p-methoxyphenyl-2,3,6-tri-O-benzyl-4-propargyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of Readily Modifiable Cyclodextrin Analogues via Cyclodimerization of an Alkynyl−Azido Trisaccharide

  摘要：

  A convergent strategy for the synthesis of beta-cyclodextrin analogues is reported, utilizing preferential cyclodimerization of an azido-alkyne trisaccharide via Cu(I)-catalyzed [3 + 2] dipolar cycloaddition of the alkyne and azide functional groups. The resultant oligosaccharide macrocycle retains the binding propensity of cyclodextrins, as demonstrated by the similar ANS association constants measured for macrocycle 1 and beta-cyclodextrin. This new synthetic strategy opens up new avenues for modular preparation of functionally diverse cyclodextrin analogues that are otherwise inaccessible.

  DOI：

  10.1021/ja039374t

文献信息

• Synthesis of Readily Modifiable Cyclodextrin Analogues via Cyclodimerization of an Alkynyl−Azido Trisaccharide
  作者：Kyle D. Bodine、David Y. Gin、Mary S. Gin

  DOI：10.1021/ja039374t

  日期：2004.2.1

  A convergent strategy for the synthesis of beta-cyclodextrin analogues is reported, utilizing preferential cyclodimerization of an azido-alkyne trisaccharide via Cu(I)-catalyzed [3 + 2] dipolar cycloaddition of the alkyne and azide functional groups. The resultant oligosaccharide macrocycle retains the binding propensity of cyclodextrins, as demonstrated by the similar ANS association constants measured for macrocycle 1 and beta-cyclodextrin. This new synthetic strategy opens up new avenues for modular preparation of functionally diverse cyclodextrin analogues that are otherwise inaccessible.