8-acetylthiooctyldodecyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside | 884508-76-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-acetylthiooctyldodecyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• CAS: 884508-76-3
• 化学式: C₃₆H₅₄O₁₉S
• 分子量: 822.879
• InChiKey: NWODCXLSZRAHOT-XPMTUQOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  56.0
• 可旋转键数：
  21.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  238.09
• 氢给体数：
  0.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  8-acetylthiooctyldodecyl 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 为溶剂， 反应 2.0h， 以82%的产率得到8-mercaptooctyl 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：

  β-D-麦芽糖八乙酸酯 在 zinc(II) chloride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.0h， 生成 8-acetylthiooctyldodecyl 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