Methyl 2,6-dideoxy-β-D-xylo-hexopyranoside | 133814-52-5

• 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-β-D-xylo-hexopyranoside
• 英文别名: (2R,3R,4S,6R)-6-methoxy-2-methyloxane-3,4-diol
• CAS: 133814-52-5
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: QNKOVWCOVLYPKR-UCROKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 2,6-dideoxy-β-D-xylo-hexopyranoside 在 吡啶 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 15.5h， 生成 Methyl 3,4-di-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranoside
  参考文献：
  名称：

  Binkley, Roger W., Journal of Carbohydrate Chemistry, 1994, vol. 13, # 1, p. 111 - 124

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R,3S,4S)-3-Benzyloxymethoxy-hept-6-ene-2,4-diol 在 钯 氢气 作用下， 以 乙醇 为溶剂， 生成 Methyl 2,6-dideoxy-β-D-xylo-hexopyranoside
  参考文献：
  名称：

  Diastereoselectivity in nucleophilic addition reactions to (.alpha.,.beta.-dialkoxyacyl) silanes: an operationally useful route to optically active 1,2,3-syn-triols

  摘要：

  DOI：

  10.1021/jo00312a005

文献信息

• CIRILLO, PIER E.;PANEK, JAMES S., J. ORG. CHEM., 55,(1990) N5, C. 6071-6073
  作者：CIRILLO, PIER E.、PANEK, JAMES S.

  DOI：——

  日期：——
• 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.
• US4086415A
  申请人：——

  公开号：US4086415A

  公开（公告）日：1978-04-25
• US4180655A
  申请人：——

  公开号：US4180655A

  公开（公告）日：1979-12-25
• Diastereoselectivity in nucleophilic addition reactions to (.alpha.,.beta.-dialkoxyacyl) silanes: an operationally useful route to optically active 1,2,3-syn-triols
  作者：Pier F. Cirillo、James S. Panek

  DOI：10.1021/jo00312a005

  日期：1990.12