methyl 2-deoxy-α-D-arabino-hexofuranoside | 6001-17-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-deoxy-α-D-arabino-hexofuranoside
• 英文别名: methyl-(α-D-arabino-2-deoxy-hexofuranoside)；Methyl-(α-D-arabino-2-desoxy-hexofuranosid)；(1R)-1-[(2S,3R,5S)-3-hydroxy-5-methoxyoxolan-2-yl]ethane-1,2-diol
• CAS: 6001-17-8
• 化学式: C₇H₁₄O₅
• 分子量: 178.185
• InChiKey: YWHNWHGHSAVRQS-JWXFUTCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-deoxy-α-D-arabino-hexofuranoside 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 methyl 2-deoxy-β-D-arabino-hexopyranoside
  参考文献：
  名称：

  甲基2-脱氧-d-阿拉伯糖-己糖苷的酸催化异构化：平衡，动力学和机理

  摘要：

  通过HPLC分离2-甲基-D-阿拉伯糖-己糖甲基的四个异构体，为色谱上均相的化合物。确定了在40摄氏度时吡喃糖苷异构化率（alpha（p）和beta（p））和在26摄氏度时呋喃糖苷异构化率（alpha（f）和beta（f））的比率。已经提出了在氯化氢催化的甲醇溶液中甲基2-脱氧-D-阿拉伯糖-己糖苷异构化过程中发生转化的机理。

  DOI：

  10.1016/s0008-6215(01)00305-6
• 作为产物：
  描述：

  methyl 2-deoxy-β-D-arabino-hexopyranoside 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 methyl 2-deoxy-α-D-arabino-hexofuranoside
  参考文献：
  名称：

  甲基2-脱氧-d-阿拉伯糖-己糖苷的酸催化异构化：平衡，动力学和机理

  摘要：

  通过HPLC分离2-甲基-D-阿拉伯糖-己糖甲基的四个异构体，为色谱上均相的化合物。确定了在40摄氏度时吡喃糖苷异构化率（alpha（p）和beta（p））和在26摄氏度时呋喃糖苷异构化率（alpha（f）和beta（f））的比率。已经提出了在氯化氢催化的甲醇溶液中甲基2-脱氧-D-阿拉伯糖-己糖苷异构化过程中发生转化的机理。

  DOI：

  10.1016/s0008-6215(01)00305-6

文献信息

• Synthesis of 2-deoxy-d-arabino-(6-13C)hexose
  作者：Thomas E. Walker、Deborah S. Ehler、Clifford J. Unkefer

  DOI：10.1016/0008-6215(88)84028-x

  日期：1988.10

  2-Deoxy-D-arabino-[6-13C]hexose (10), to be used to test the stability of 2-deoxy-D-arabino-hexose 6-phosphate in brain tissue, was prepared. 2-Deoxy-D-arabino-hexose was labeled at C-6 because of the large difference in chemical shift between C-6 in the free sugar and C-6 in the 6-phosphate. The synthetic scheme resembled that used for the synthesis of D-[6-13C]glucose that involved the removal of C-6 from D-glucose followed by its replacement with 13C. The protected derivative methyl 2-deoxy-alpha-D-arabino-hexofuranoside was prepared, using trifluoroacetic acid in methanol. This was treated with periodate, which cleaves only between C-5 and C-6, to afford an aldehyde which reacted directly with K13CN to give a mixture of the D-arabino and L-xylo nitriles. The enriched nitriles were reduced with hydrogen in the presence of 5% Pd-carbon catalyst to a mixture of 6-aldehydo sugars. These were reduced with NaBH4 to a mixture of the two labeled methyl furanosides. Acid hydrolysis followed by ion-exchange chromatography on AG-50(Ca2+) resin at 65 degrees gave 10 in an overall yield of 16% from K13CN.
• Hughes et al., Journal of the Chemical Society, 1949, p. 2846,2848
  作者：Hughes et al.

  DOI：——

  日期：——
• 2-Deoxy sugars
  作者：K.V. Bhat、W.Werner Zorbach

  DOI：10.1016/s0008-6215(00)80217-7

  日期：1965.7
• Synthesis of methyl 3,5-di-O-benzoyl-2,6-dideoxy-β-l-lyxo-hexofuranoside, a nucleoside precursor
  作者：Victor Nelson、Hassan S. El Khadem

  DOI：10.1016/0008-6215(83)88365-7

  日期：1983.12
• Acid-catalyzed isomerization of methyl 2-deoxy-d-arabino-hexosides: equilibria, kinetics and mechanism
  作者：Andrzej Nowacki、Kazimiera Smiataczowa、Regina Kasprzykowska、Barbara Dmochowska、Andrzej Wiśniewski

  DOI：10.1016/s0008-6215(01)00305-6

  日期：2002.2

  isolated by HPLC as chromatographically homogeneous compounds. The rates of pyranoside isomerization (alpha(p) and beta(p)) at 40 degrees C and of furanoside isomerization (alpha(f) and beta(f)) at 26 degrees C were determined. A mechanism has been suggested for transformations taking place during isomerization of methyl 2-deoxy-D-arabino-hexosides in methanolic solution catalyzed with hydrogen chloride

  通过HPLC分离2-甲基-D-阿拉伯糖-己糖甲基的四个异构体，为色谱上均相的化合物。确定了在40摄氏度时吡喃糖苷异构化率（alpha（p）和beta（p））和在26摄氏度时呋喃糖苷异构化率（alpha（f）和beta（f））的比率。已经提出了在氯化氢催化的甲醇溶液中甲基2-脱氧-D-阿拉伯糖-己糖苷异构化过程中发生转化的机理。