3,4-di-O-acetyl-1,6-dibromo-1,6-dideoxy-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-4-bromo-4-deoxy-α-D-glucopyranoside | 361553-25-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-di-O-acetyl-1,6-dibromo-1,6-dideoxy-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-4-bromo-4-deoxy-α-D-glucopyranoside
• 英文别名: [(2R,3R,4R,5R,6R)-4,5-diacetyloxy-3-bromo-6-[(2R,3S,4S,5S)-3,4-diacetyloxy-2,5-bis(bromomethyl)oxolan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 361553-25-5
• 化学式: C₂₂H₂₉Br₃O₁₃
• 分子量: 741.176
• InChiKey: WHHYCVQYKFMQIS-ZQNATQRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  159
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  3,4-di-O-acetyl-1,6-dibromo-1,6-dideoxy-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-4-bromo-4-deoxy-α-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以87%的产率得到1,6-dibromo-1,6-dideoxy-β-D-fructofuranosyl 4-bromo-4-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  SYNTHESIS AND TASTE PROPERTIES OF 4,1′, 6′-TRIHALODEOXY SUCROSE ANALOGUES1-2

  摘要：

  Treatment of 3,4-di-O-acetyl-1,6-di-O-trityl-beta -D-fructofuranosyl 2,3,6-tri-O-acetyl-4-O-triflyl-alpha -D-galactopyranoside (3) with a halide source gave, via S(N)2 displacement, the corresponding C-4 halogenated compounds which were subsequently transformed into the monohalogenated 4-deoxy-4-halogenosucrose derivatives, 10-12. Trihalogenated sucrose derivatives, 4-bromo-1',6'- dichloro 17, 1',6'-dibromo 18, and 1',6'-diiodosucrose 19, were synthesized from 5. Exploiting the distinct reactivity at C-1' and C-6' trifluoromethanesulfonates enabled the introduction of different halogens at these positions. This pathway led to the preparation of the 4-bromo-1',6'-dihalodeoxysucrose derivatives, 24-27. Preliminary taste properties of these mono- and tri-halogenated sucrose analogues were also investigated.

  DOI：

  10.1081/car-100103958
• 作为产物：
  描述：

  3,4-di-O-acetyl-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-4-bromo-4-deoxy-α-D-glucopyranoside 在 吡啶 、 lithium bromide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 3,4-di-O-acetyl-1,6-dibromo-1,6-dideoxy-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-4-bromo-4-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  SYNTHESIS AND TASTE PROPERTIES OF 4,1′, 6′-TRIHALODEOXY SUCROSE ANALOGUES1-2

  摘要：

  Treatment of 3,4-di-O-acetyl-1,6-di-O-trityl-beta -D-fructofuranosyl 2,3,6-tri-O-acetyl-4-O-triflyl-alpha -D-galactopyranoside (3) with a halide source gave, via S(N)2 displacement, the corresponding C-4 halogenated compounds which were subsequently transformed into the monohalogenated 4-deoxy-4-halogenosucrose derivatives, 10-12. Trihalogenated sucrose derivatives, 4-bromo-1',6'- dichloro 17, 1',6'-dibromo 18, and 1',6'-diiodosucrose 19, were synthesized from 5. Exploiting the distinct reactivity at C-1' and C-6' trifluoromethanesulfonates enabled the introduction of different halogens at these positions. This pathway led to the preparation of the 4-bromo-1',6'-dihalodeoxysucrose derivatives, 24-27. Preliminary taste properties of these mono- and tri-halogenated sucrose analogues were also investigated.

  DOI：

  10.1081/car-100103958