3,4-di-O-tert-butyldiphenylsilyl-2,6-dideoxy-D-ribo-hexopyranosyl o-cyclopropylethynylbenzoate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-di-O-tert-butyldiphenylsilyl-2,6-dideoxy-D-ribo-hexopyranosyl o-cyclopropylethynylbenzoate
• 英文别名: [(4S,5R,6R)-4,5-bis[[tert-butyl(diphenyl)silyl]oxy]-6-methyloxan-2-yl] 2-(2-cyclopropylethynyl)benzoate
• 化学式: C₅₀H₅₆O₅Si₂
• 分子量: 793.163
• InChiKey: GFJRBZAGCNPFPB-VSRRLONKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.63
• 重原子数：
  57
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  digitoxigen O-[3'-O-acetyl-2',6'-dideoxy-β-D-ribo-hexopyranosyl]-(1->4)-(3-O-acetyl-2,6-dideoxy-β-D-ribo-hexopyranoside) 、 3,4-di-O-tert-butyldiphenylsilyl-2,6-dideoxy-D-ribo-hexopyranosyl o-cyclopropylethynylbenzoate 在 trifluoromethanesulfonyloxy(triphenylphosphine)gold(I) 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 以97%的产率得到digitoxigenin 3''',4'''-di-O-tert-butyldiphenylsilyl-2''',6'''-dideoxy-β-D-ribo-hexopyranosyl-(1->4)-3''-O-acetyl-2'',6''-dideoxy-β-D-ribo-hexopyranosyl-(1->4)-3'-O-acetyl-2',6'-dideoxy-β-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.