12-bromododecyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside | 884508-72-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 12-bromododecyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-(12-bromododecoxy)-3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 884508-72-9
• 化学式: C₃₈H₅₉BrO₁₈
• 分子量: 883.78
• InChiKey: MWTSSSSQHITUMG-JQYMQLFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  57
• 可旋转键数：
  31
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  221
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  12-bromododecyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 12-mercaptododecyl α-D-glucopyranosyl-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Efficient synthesis of ω-mercaptoalkyl 1,2-trans-glycosides from sugar peracetates

  摘要：

  Lewis acid-promoted reactions of peracetylated sugars (glucose, galactose, maltose, lactose) with omega-bromo-1-alkanols (C-8, C-12) were investigated. ZnCl2, was found to promote the 1,2-trans-glycosylation of the alcohols in toluene at about 60 degrees C in a stereocontrolled manner with better yields than commonly employed promoters such as SnCl4. The omega-bromoalkyl acetylated glycosides were readily converted to omega-mercaptoalkyl glycosides, which are useful for the preparation of glycoclusters. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.02.024
• 作为产物：
  描述：

  12-溴-1-十二烷醇 、 β-D-麦芽糖八乙酸酯 在 zinc(II) chloride 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以46%的产率得到12-bromododecyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Efficient synthesis of ω-mercaptoalkyl 1,2-trans-glycosides from sugar peracetates

  摘要：

  Lewis acid-promoted reactions of peracetylated sugars (glucose, galactose, maltose, lactose) with omega-bromo-1-alkanols (C-8, C-12) were investigated. ZnCl2, was found to promote the 1,2-trans-glycosylation of the alcohols in toluene at about 60 degrees C in a stereocontrolled manner with better yields than commonly employed promoters such as SnCl4. The omega-bromoalkyl acetylated glycosides were readily converted to omega-mercaptoalkyl glycosides, which are useful for the preparation of glycoclusters. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.02.024