methyl 2-deoxy-3-O-(p-methoxybenzoyl)-α-D-ribo-hexopyranoside | 1345697-20-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-deoxy-3-O-(p-methoxybenzoyl)-α-D-ribo-hexopyranoside
• 英文别名: I+/--D-ribo-Hexopyranoside, methyl 2-deoxy-, 3-(4-methoxybenzoate)；[(2R,3S,4S,6S)-3-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl] 4-methoxybenzoate
• CAS: 1345697-20-2
• 化学式: C₁₅H₂₀O₇
• 分子量: 312.32
• InChiKey: XQRKQSSFAKVHEE-CRWXNKLISA-N

物化性质

• 沸点：
  497.6±45.0 °C(predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-deoxy-3-O-(p-methoxybenzoyl)-α-D-ribo-hexopyranoside 在 咪唑 、 水 、 碘 、 溶剂黄146 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 11.0h， 生成 2,6-dideoxy-3,4-bis-O-(p-methoxybenzoyl)-D-ribo-hexose
  参考文献：
  名称：

  Assembly of Digitoxin by Gold(I)-Catalyzed Glycosidation of Glycosyl o-Alkynylbenzoates

  摘要：

  Digitoxin, a clinically important cardiac trisactharicle, was assembled efficiently from digitoxigenin and 3,4-di-O-tert-butyldiphenylsilyl-D-digitoxosyl o-cyclopropylethynyl-benzoate in 9 steps and 52% overall yield via alternate glycosylation and protecting group manipulation. The present synthesis showcases the advantage of the gold(I)-catalyzed glycosylation protocol in the synthesis of glycoconjugates containing acid-labile 2-deoxysugar linkages.

  DOI：

  10.1021/jo201850z
• 作为产物：
  描述：

  methyl 4,6-di-O-benzylidene-2,3-di-O-tosyl-α-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 sodium methylate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 8.0h， 生成 methyl 2-deoxy-3-O-(p-methoxybenzoyl)-α-D-ribo-hexopyranoside
  参考文献：
  名称：

  Assembly of Digitoxin by Gold(I)-Catalyzed Glycosidation of Glycosyl o-Alkynylbenzoates

  摘要：

  Digitoxin, a clinically important cardiac trisactharicle, was assembled efficiently from digitoxigenin and 3,4-di-O-tert-butyldiphenylsilyl-D-digitoxosyl o-cyclopropylethynyl-benzoate in 9 steps and 52% overall yield via alternate glycosylation and protecting group manipulation. The present synthesis showcases the advantage of the gold(I)-catalyzed glycosylation protocol in the synthesis of glycoconjugates containing acid-labile 2-deoxysugar linkages.

  DOI：

  10.1021/jo201850z

文献信息

• Assembly of Digitoxin by Gold(I)-Catalyzed Glycosidation of Glycosyl <i>o</i>-Alkynylbenzoates
  作者：Yuyong Ma、Zhongzhen Li、Hefang Shi、Jian Zhang、Biao Yu

  DOI：10.1021/jo201850z

  日期：2011.12.2

  Digitoxin, a clinically important cardiac trisactharicle, was assembled efficiently from digitoxigenin and 3,4-di-O-tert-butyldiphenylsilyl-D-digitoxosyl o-cyclopropylethynyl-benzoate in 9 steps and 52% overall yield via alternate glycosylation and protecting group manipulation. The present synthesis showcases the advantage of the gold(I)-catalyzed glycosylation protocol in the synthesis of glycoconjugates containing acid-labile 2-deoxysugar linkages.