methyl 3,4-di-O-tert-butyldiphenylsilyl-2,6-dideoxy-α-D-ribo-hexopyranoside | 1345697-38-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4-di-O-tert-butyldiphenylsilyl-2,6-dideoxy-α-D-ribo-hexopyranoside
• 英文别名: TBDPS(-3)[TBDPS(-4)]a-Dig1Me；tert-butyl-[(2R,3R,4S,6S)-3-[tert-butyl(diphenyl)silyl]oxy-6-methoxy-2-methyloxan-4-yl]oxy-diphenylsilane
• CAS: 1345697-38-2
• 化学式: C₃₉H₅₀O₄Si₂
• 分子量: 638.995
• InChiKey: SAPTWRXNHYFAKT-WGKBJPKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.66
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3,4-di-O-tert-butyldiphenylsilyl-2,6-dideoxy-α-D-ribo-hexopyranoside 在 水 、 溶剂黄146 作用下， 反应 4.0h， 生成
  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：

  叔丁基二苯基氯硅烷 、 methyl 2,6-dideoxy-α-D-ribo-hexopyranoside 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以100%的产率得到methyl 3,4-di-O-tert-butyldiphenylsilyl-2,6-dideoxy-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.