3,4-di-O-acetyl-1,6-di-O-trityl-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-α-D-galactopyranoside | 361531-48-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3,4-di-O-acetyl-1,6-di-O-trityl-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-α-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-4,5-diacetyloxy-6-[(2S,3S,4R,5R)-3,4-diacetyloxy-2,5-bis(trityloxymethyl)oxolan-2-yl]oxy-3-hydroxyoxan-2-yl]methyl acetate
• CAS: 361531-48-8
• 化学式: C₆₀H₆₀O₁₆
• 分子量: 1037.13
• InChiKey: JVQFCSHWZXHOJO-NFFUQTNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  76
• 可旋转键数：
  25
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  198
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  3,4-di-O-acetyl-1,6-di-O-trityl-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-α-D-galactopyranoside 在 吡啶 、 盐酸 、 sodium methylate 、 lithium bromide 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 丙酮 为溶剂， 反应 10.0h， 生成 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-1,6-di-O-trityl-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-α-D-glucopyranoside 在 吡啶 、 sodium nitrite 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 3,4-di-O-acetyl-1,6-di-O-trityl-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-α-D-galactopyranoside
  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

文献信息

• C-4 EPIMERIZATION OF α-D-GLUCOPYRANOSIDE: A FACILE SYNTHESIS OF 4-<i>O</i>-ACETYL-α-D-GALACTOPYRANOSYL DERIVATIVES
  作者：A. S. Md. Sofian、C. Kuan Lee

  DOI：10.1081/car-100106926

  日期：2001.7.31

  An unexpected epimerization resulting from the reaction of alpha -D-glucopyranosyl derivatives with DAST is described. The reaction of 3,4-di-O-acetyl-1,6-di-O-trityl-beta -D-fructofuranosyl 2,3,6-tri-O-acetyl-alpha -D-glucopyranoside (1), methyl 2,3-di-O-acetyl-6-O-trityl-alpha -D-glucopyranoside (6), 2,3-di-O-acetyl-6-O-trityl-alpha -D-glucopyranosyl 2,3-di-O-acetyl-6-0-trityl-alpha -D-glucopyranoside (13), and 2,3-di-O-acetyl-6-O-tert-butyldiphenylsilyl-alpha -D-glucopyranosyl 2,3,4,6-tetra-O-acetyl-alpha -D-glucopyranoside (14) with DAST at 0 degreesC did not give the expected C-4 fluorodeoxy galacto derivatives, but instead, the corresponding 4-O-acetyl-3-hydroxy-alpha -D-galactopyranosides in yields of 52-78%. When the treatment of 6 was carried out at -25 degreesC for similar to5 min the corresponding diastereomeric 4-O-diethylaminosulfinates (9a,b) were isolated as the major products (40%). Evidence suggests that the epimerization reaction most probably resulted from an intramolecular displacement of the intermediate diethylaminosulfur difluoride ester or diethylaminosulfinyl ester by the neighbouring acetoxy groups.