methyl 3-amino-3-deoxy-β-D-xylofuranoside | 64623-02-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-amino-3-deoxy-β-D-xylofuranoside
• 英文别名: methyl-[3-amino-3-deoxy-β-D-xylofuranoside；Methyl-[3-amino-3-desoxy-β-D-xylofuranosid；(2R,3R,4R,5S)-4-amino-5-(hydroxymethyl)-2-methoxyoxolan-3-ol
• CAS: 64623-02-5
• 化学式: C₆H₁₃NO₄
• 分子量: 163.174
• InChiKey: VHIPCQWVLTUVSP-JGWLITMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-amino-3-deoxy-β-D-xylofuranoside 在 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 methyl 3-deoxy-3-diallylamino-2,5-di-O-methylsulfonyl-β-D-xylofuranoside
  参考文献：
  名称：

  Fluorination by anchimeric assistance of a diallylamino group: application to the synthesis of some methyl aminofluoropentofuranosides

  摘要：

  Methyl 2,3-trans-dialkylaminofluoro-alpha(or beta)-D-pentofuranosides were prepared by fluorination wherein the dialkylamino, group assists the replacement of a trans-vicinal mesylate. Whatever the location of the dialkylamino group (alpha or beta face of the ring), the regioselectivity of fluorination depends mainly on the alpha or beta orientation of the anomeric methoxyl group. The use of a diallylamino substituent led to methyl 3-amino-2,3-dideoxy-2-fluoro-beta-D-xylofuranoside, methyl 2-amino-2,3-dideoxy-3-fluoro-alpha-D-arabinofuranoside, methyl 2-amino-2,3-dideoxy-3-fluoro-beta-D-xylofuranoside, and methyl 3-amino-2,3-dideoxy-2-fluoro-alpha-D-arabinofuranoside. Attempts to obtain 2(or 3),5-difluoro analogues staring from corresponding dimesylates gave only disappointing results.

  DOI：

  10.1016/0008-6215(93)84057-d
• 作为产物：
  描述：

  2,3-anhydro-β-D-ribofuranoside de methyle 在 ammonium hydroxide 作用下， 反应 16.0h， 以100%的产率得到methyl 3-amino-3-deoxy-β-D-xylofuranoside
  参考文献：
  名称：

  Fluorination by anchimeric assistance of a diallylamino group: application to the synthesis of some methyl aminofluoropentofuranosides

  摘要：

  Methyl 2,3-trans-dialkylaminofluoro-alpha(or beta)-D-pentofuranosides were prepared by fluorination wherein the dialkylamino, group assists the replacement of a trans-vicinal mesylate. Whatever the location of the dialkylamino group (alpha or beta face of the ring), the regioselectivity of fluorination depends mainly on the alpha or beta orientation of the anomeric methoxyl group. The use of a diallylamino substituent led to methyl 3-amino-2,3-dideoxy-2-fluoro-beta-D-xylofuranoside, methyl 2-amino-2,3-dideoxy-3-fluoro-alpha-D-arabinofuranoside, methyl 2-amino-2,3-dideoxy-3-fluoro-beta-D-xylofuranoside, and methyl 3-amino-2,3-dideoxy-2-fluoro-alpha-D-arabinofuranoside. Attempts to obtain 2(or 3),5-difluoro analogues staring from corresponding dimesylates gave only disappointing results.

  DOI：

  10.1016/0008-6215(93)84057-d

文献信息

• The Synthesis of the Four Possible Methyl 3-Amino-3-deoxy-D-xylosides. A Novel Ring Expansion of a Furanoside to a Pyranoside
  作者：Robert E. Schaub、Martin J. Weiss

  DOI：10.1021/ja01550a066

  日期：1958.9
• Potential Anticancer Agents.¹ VII. Synthesis and Ammonolysis of Methyl 2,3-Anhydro-D-ribofuranoside
  作者：Charles D. Anderson、Leon Goodman、B. R. Baker

  DOI：10.1021/ja01552a057

  日期：1958.10