(E)-1,2-Dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-D-gluco-hexo-1-enose | 138459-03-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1,2-Dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-D-gluco-hexo-1-enose
• CAS: 138459-03-7；138514-62-2
• 化学式: C₃₇H₄₆O₉
• 分子量: 634.767
• InChiKey: MRZOCFVKRWJPJI-CGSXKODISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  46.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  105.07
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (E)-1,2-Dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-D-gluco-hexo-1-enose 、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以89%的产率得到(Z)-6-O-(tert-Butyldiphenylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-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：

  2,3-O-isopropylidene-D-arabinose diethyl dithio acetal 在 咪唑 、 2,6-二甲基吡啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 18.17h， 生成 (E)-1,2-Dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-D-gluco-hexo-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