methyl 3,5-anhydro-2,6-dideoxy-β-D-xylo-hexofuranoside | 139656-50-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: methyl 3,5-anhydro-2,6-dideoxy-β-D-xylo-hexofuranoside
• 英文别名: (1S,3R,5S,7R)-3-methoxy-7-methyl-2,6-dioxabicyclo[3.2.0]heptane
• CAS: 139656-50-1
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: ZNKOBOFXIDQXRS-UCROKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 2,6-dideoxy-β-D-ribo-hexopyranoside 在 2,6-二叔丁基-4-甲基吡啶 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 1.0h， 生成 methyl 3,5-anhydro-2,6-dideoxy-β-D-xylo-hexofuranoside
  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

文献信息

• Intramolecular reactions of carbohydrate triflates
  作者：Roger W. Binkley

  DOI：10.1021/jo00034a030

  日期：1992.4

  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.