2-Bromo-6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1,2-dideoxy-1-C-<(tert-butyldiphenylsiloxy)methyl>-β-D-gluco-hexapyranose | 138458-99-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Bromo-6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1,2-dideoxy-1-C-<(tert-butyldiphenylsiloxy)methyl>-β-D-gluco-hexapyranose
• 英文别名: 2-Bromo-6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1,2-dideoxy-1-C-[(tert-butyldiphenylsiloxy)methyl]-β-D-gluco-hexapyranose
• CAS: 138458-99-8
• 化学式: C₄₂H₅₃BrO₅Si₂
• 分子量: 773.955
• InChiKey: WRCZAIARWGCMHU-VTNNJHASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.19
• 重原子数：
  50.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (E)-6-O-(tert-Butyldiphenylsilyl)-3,4-O-isopropylidene-1,2-dideoxy-1-<(tert-butyldiphenylsiloxy)methyl>-D-gluco-hex-1-enose 在 N-溴代丁二酰亚胺(NBS) 、 溴 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以52%的产率得到2-Bromo-6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1,2-dideoxy-1-C-<(tert-butyldiphenylsiloxy)methyl>-β-D-gluco-hexapyranose
  参考文献：
  名称：

  Synthesis of .alpha.-methyl 1',2'-dideoxycellobioside: a novel C-disaccharide

  摘要：

  Bromonium ion induced 6-endo-trig cyclizations of E olefine derived from D-arabinose provide a stereoselective route to 2'-deoxyglucono-beta-C-glycosides. Use of delta-alkenols containing allylic isopropylidenes (i.e., 1) prevents formation of furan products due to the highly strained transition state necessary for formation of the trans [3.3.0] bicyclic systems. Because the exo-anomeric carbon is not involved in the cyclization, previously established stereocenters at this carbon are left intact. Application of this methodology to the synthesis of alpha-methyl 1',2'-dideoxycellobioside (22) is presented. The restricted rotation about the bond connecting the two sugars affords a unique staggared conformation of the disaccharide.

  DOI：

  10.1021/jo00029a024