methyl 2,6-dideoxy-4-O-<(trifluoromethyl)sulfonyl>-3-O-(trimethylsilyl)-β-D-xylo-hexopyranoside | 139656-51-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,6-dideoxy-4-O-<(trifluoromethyl)sulfonyl>-3-O-(trimethylsilyl)-β-D-xylo-hexopyranoside
• 英文别名: [(2R,3S,4S,6R)-6-methoxy-2-methyl-4-trimethylsilyloxyoxan-3-yl] trifluoromethanesulfonate
• CAS: 139656-51-2
• 化学式: C₁₁H₂₁F₃O₆SSi
• 分子量: 366.431
• InChiKey: NLRLKEWHMDNODO-RGOKHQFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.22
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  三氟甲磺酸酐 、 三氟甲磺酸三甲基硅酯 、 Methyl 2,6-dideoxy-β-D-xylo-hexopyranoside 在 2,6-二叔丁基-4-甲基吡啶 作用下， 生成 methyl 2,6-dideoxy-4-O-<(trifluoromethyl)sulfonyl>-3-O-(trimethylsilyl)-β-D-xylo-hexopyranoside 、 Methyl 3,4-anhydro-2,6-dideoxy-β-D-lyxo-hexopyranoside
  参考文献：
  名称：

  Intramolecular reactions of carbohydrate triflates

  摘要：

  Each of the four possible methyl 2,6-dideoxy-beta-D-hexopyranosides (3-6) was treated with an equivalent amount of triflic anhydride in the presence of 2,6-di-tert-butyl-4-methylpyridine (7). The ribo isomer 3 produced both the 3-O-triflyl (8, 15%) and the 4-O-triflyl (9, 73%) derivatives while the lyxo isomer 4 gave only the 3-O-triflyl compound (11, 84%). Upon heating, the triflate 8 lost the elements of triflic acid to form methyl 2,3,6-trideoxy-beta-D-glycero-hexopyranosid-4-ulose (23, 72%), while 9 experienced ring contraction involving the pyranoid ring oxygen to form methyl 3,5-anhydro-2,6-dideoxy-beta-D-xylo-hexofuranoside (20, 54%). Compound 11 produced methyl 3-C-aldehydo-2,5-dideoxy-beta-D-threo-pentofuranoside (13, 65%). Upon reaction with triflic anhydride, methyl 2,6-dideoxy-beta-D-arabino- and -xylo-hexopyranosides (5 and 6, respectively) generated hydroxy triflates which were not isolated due to their further reaction below room temperature. Compound 5 produced aldehyde 13 (54%) while reaction of 6 gave methyl 3,4-anhydro-2,6-dideoxy-beta-D-lyxo- and -ribo-hexopyranosides [15 (48%) and 16 (24%), respectively]. The mechanisms for these reactions are discussed and the reactivity of the hydroxy triflates is compared to that of related carbohydrate derivatives.

  DOI：

  10.1021/jo00034a030