4'-bromo-4'-deoxysucrose | 111829-10-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4'-bromo-4'-deoxysucrose
• CAS: 111829-10-8
• 化学式: C₁₂H₂₁BrO₁₀
• 分子量: 405.197
• InChiKey: PSSDEYGYFZJDBW-UGDNZRGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.99
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  169.3
• 氢给体数：
  7.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  3,6'-di-O-acetyl-3',4'-anhydro-4,6:2,1'-di-O-isopropylidene-"tagatosucrose" 在 氢溴酸 、 sodium methylate 、 溶剂黄146 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 54.2h， 生成 4'-bromo-4'-deoxysucrose
  参考文献：
  名称：

  Ring-opening reactions of sucrose epoxides: Synthesis of 4′-derivatives of sucrose

  摘要：

  The 2,1''-O-isopropylidene derivative (1) of 3-O-acetyl-4,6-O-isopropylidene-.alpha.-D-glucopyranosyl 6-O-acetyl-3,4-anhydro-.beta.-D-lyxo-hexulofuranoside and 2,3,4-tri-O-acetyl-6-O-trityl-.alpha.-D-glucopyranosyl 3,4-anhydro-1,6-di-O-trityl-.beta.-D-lyxo-hexulofuranoside have been synthesised and 1 has been converted into 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl 1,6-di-O-acetyl-3,4-anhydro-.beta.-D-lyxo-hexulofuranoside (2). The SN2 reactions of 2 with azide and chloride nucleophiles gave the corresponding 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl 1,3,6-tri-O-acetyl-4-azido-4-deoxy-.beta.-D-fructofuranoside (6) and 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl 1,3,6-tri-O-acetyl-4-chloro-4-deoxy-.beta.-D-fructofuranoside (8), respectively. The azide 6 was catalytically hydrogenated and the resulting amine was isolated as 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl 4-acetamido-1,3,6-tri-O-acetyl-4-deoxy-.beta.-D-fructofuranoside. Treatment of 5 with hydrogen bromide in glacial acetic acid followed by conventional acetylation gave 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl 1,3,6-tri-O-acetyl-4-bromo-4-deoxy-.beta.-D-fructofuranoside. Similar SN2 reactions with 2,3,4,6-tetra-O-acetyl-.alpha.-D-glucopyranosyl 1,6-di-O-acetyl-3,4-anhydro-.beta.-D-ribo-hexulofuranoside (12) resulted in a number of 4''-derivatives of .alpha.-D-glucopyranosyl .beta.-D-sorbofuranoside. The regiospecific nucleophilic substitution at position 4'' in 2 and 12 has been explained on the basis of steric and polar factors.

  DOI：

  10.1016/0008-6215(87)80215-x