(E)-5-O-Acetyl-6-O-(tert-butyldiphenylsilyl)-1-formyl-3,4-O-isopropylidene-1,2-dideoxy-D-gluco-hex-1-enose | 138458-97-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-5-O-Acetyl-6-O-(tert-butyldiphenylsilyl)-1-formyl-3,4-O-isopropylidene-1,2-dideoxy-D-gluco-hex-1-enose
• CAS: 138458-97-6
• 化学式: C₂₈H₃₆O₆Si
• 分子量: 496.676
• InChiKey: WGOPVVMIQOXXGE-ONWBVMNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (E)-5-O-Acetyl-6-O-(tert-butyldiphenylsilyl)-1-formyl-3,4-O-isopropylidene-1,2-dideoxy-D-gluco-hex-1-enose 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.42h， 以99%的产率得到(E)-6-O-(tert-Butyldiphenylsilyl)-3,4-O-isopropylidene-1,2-dideoxy-1-(hydroxymethyl)-D-gluco-hex-1-enose
  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
• 作为产物：
  描述：

  4-O-Acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-arabinose diethyl dithioacetal 在 2,6-二甲基吡啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 12.17h， 生成 (E)-5-O-Acetyl-6-O-(tert-butyldiphenylsilyl)-1-formyl-3,4-O-isopropylidene-1,2-dideoxy-D-gluco-hex-1-enose
  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