Acetic acid (2S,3S,4R,5R)-4-acetoxy-2-((2R,3R,4R,5R,6R)-3,4-diacetoxy-6-acetoxymethyl-5-bromo-tetrahydro-pyran-2-yloxy)-2,5-bis-trifluoromethanesulfonyloxymethyl-tetrahydro-furan-3-yl ester | 361531-58-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2S,3S,4R,5R)-4-acetoxy-2-((2R,3R,4R,5R,6R)-3,4-diacetoxy-6-acetoxymethyl-5-bromo-tetrahydro-pyran-2-yloxy)-2,5-bis-trifluoromethanesulfonyloxymethyl-tetrahydro-furan-3-yl ester
• CAS: 361531-58-0
• 化学式: C₂₄H₂₉BrF₆O₁₉S₂
• 分子量: 879.509
• InChiKey: YFPLKGGOYGGVJJ-ZQNATQRZSA-N

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3S,4R,5R)-4-acetoxy-2-((2R,3R,4R,5R,6R)-3,4-diacetoxy-6-acetoxymethyl-5-bromo-tetrahydro-pyran-2-yloxy)-2,5-bis-trifluoromethanesulfonyloxymethyl-tetrahydro-furan-3-yl ester 在 sodium methylate 、 lithium bromide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 4.0h， 生成 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-1,6-di-O-trityl-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-4-bromo-4-deoxy-α-D-glucopyranoside 在 吡啶 、 盐酸 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 2.0h， 生成 Acetic acid (2S,3S,4R,5R)-4-acetoxy-2-((2R,3R,4R,5R,6R)-3,4-diacetoxy-6-acetoxymethyl-5-bromo-tetrahydro-pyran-2-yloxy)-2,5-bis-trifluoromethanesulfonyloxymethyl-tetrahydro-furan-3-yl ester
  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