2,6-dideoxy-3,4-di-O-(p-methoxybenzoyl)-β-D-ribo-hexopyranosyl o-(cyclopropylethynyl)benzoate | 1345697-29-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-dideoxy-3,4-di-O-(p-methoxybenzoyl)-β-D-ribo-hexopyranosyl o-(cyclopropylethynyl)benzoate
• 英文别名: [(2S,4S,5R,6R)-4,5-bis[(4-methoxybenzoyl)oxy]-6-methyloxan-2-yl] 2-(2-cyclopropylethynyl)benzoate
• CAS: 1345697-29-1
• 化学式: C₃₄H₃₂O₉
• 分子量: 584.623
• InChiKey: IPQSQBLKBPUUBC-VIBPWNLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,6-dideoxy-3,4-di-O-(p-methoxybenzoyl)-β-D-ribo-hexopyranosyl o-(cyclopropylethynyl)benzoate 、 毛地黄毒苷配基 在 trifluoromethanesulfonyloxy(triphenylphosphine)gold(I) 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 digitoxigenin 2,6-dideoxy-3,4-di-O-(p-methoxybenzoyl)-β-D-ribo-hexopyranoside 、 digitoxigenin 2,6-dideoxy-3,4-di-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
• 作为产物：
  描述：

  methyl 4,6-di-O-benzylidene-2,3-di-O-tosyl-α-D-glucopyranoside 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 水 、 碘 、 sodium methylate 、 对甲苯磺酸 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 19.0h， 生成 2,6-dideoxy-3,4-di-O-(p-methoxybenzoyl)-β-D-ribo-hexopyranosyl o-(cyclopropylethynyl)benzoate 、 2,6-dideoxy-3,4-di-O-(p-methoxybenzoyl)-α-D-ribo-hexopyranosyl o-(cyclopropylethynyl)benzoate
  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.