3,5-di-O-methyl-α,β-D-xylofuranose | 3253-82-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-di-O-methyl-α,β-D-xylofuranose
• 英文别名: 3,5-di-O-methyl-D-xylofuranose；(3R,4R,5R)-4-methoxy-5-(methoxymethyl)oxolane-2,3-diol
• CAS: 3253-82-5
• 化学式: C₇H₁₄O₅
• 分子量: 178.185
• InChiKey: OYSGGZXRZAPJTA-FTFTVQOISA-N

物化性质

• 沸点：
  296.0±40.0 °C(predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 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：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-di-O-methyl-α,β-D-xylofuranose 在 lithium hydroxide 、 ammonium chloride 、 2-氯-1-甲基吡啶碘化物 、 sodium hydride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 1-N-[5',6'-trans-2',2',4',4'-tetramethyl-1'-aza-3'-thio-bicyclo[3.2.0]-heptan-7'-onyl]-1-N,2-O-carbonyl-3,5-di-O-methyl-α-D-xylofuranosylamine
  参考文献：
  名称：

  基于d-木糖的新型手性恶唑烷酮助剂的合成及其在施陶丁格反应中的应用

  摘要：

  描述了基于d​​-木糖的新型手性恶唑烷酮助剂的合成，其用于非对映选择性施陶丁格型β-内酰胺合成中。使用2-氯-1-甲基碘化碘作为脱水剂，辅助束缚乙酸与无环或环状亚胺的反应可制得所需的β-内酰胺，产率高，取决于亚胺的几何构型，具有优异的顺式或反式选择性。所得化合物之一的X射线结构测定证实了所有顺式产物的绝对构型。

  DOI：

  10.1016/s0957-4166(99)00506-6
• 作为产物：
  描述：

  1,2-O-异亚丙基-alpha-D-呋喃木糖 在 Amberlite IR 120 (H⁺) 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 76.0h， 生成 3,5-di-O-methyl-α,β-D-xylofuranose
  参考文献：
  名称：

  D-XYLOSE (D-GLUCOSE) ISOMERASE (EC 5.3.1.5): OBSERVATIONS AND COMMENTS CONCERNING STRUCTURAL REQUIREMENTS OF SUBSTRATES AS WELL AS MECHANISTIC FEATURES

  摘要：

  In the course of investigations into the applicability of xylose isomerase as a reagent for carbohydrate synthesis, some questions raised in context with structural requirements for productive substrates as well as mechanistic considerations have been addressed. Amongst the interesting findings obtained so far is the observation that the enzyme requires two vicinal hydroxyl groups, either at positions C-3 and C-4 or at C-4 and C-5, for productive binding/catalysis. Furthermore, two apparently different reaction pathways occur in parallel when certain aldopentoses as well as selected aldohexoses are offered as substrates, this explaining the recently observed formation of epimeric aldoses together with the expected ketoses observed upon extended reaction times.

  DOI：

  10.1081/car-100104860

文献信息

• Synthèse de nucléosides pyrimidiques non protégés en O-2′ à partir de sulfites cycliques en C-1—C-2
  作者：Christian H. Gagnieu、Alain Guiller、Henri Pacheco

  DOI：10.1016/0008-6215(88)80080-6

  日期：1988.9

  was readily hydrolyzed in slightly acid conditions to give in almost quantitative yield 1-(3,5,6-tri- O -benzoyl-β- d -glucofuranosyl)uracil. This new synthetic method for nucleosides unprotected at O-2′ was also tested in other sugar series. In some cases, only the 1′,2′- trans -nucleosides were obtained, but in others, small yields (3–10%) of 1′,2′- cis -nucleosides were detected. The α-to-β ratio

  摘要在没有任何催化剂的熔融过程中，用过量的双（三甲基硅）尿嘧啶处理3,5,6-三-O-苯甲酰基-α-d-葡萄糖呋喃糖1,2-亚硫酸盐，得到了1-（-）极好的收率。 3,5,6-三-O-苯甲酰基-2-O-三甲基甲硅烷基-β-d-葡萄糖基呋喃糖基）尿嘧啶，在弱酸性条件下容易水解，几乎可以定量得到1-（3,5,6-tri -O-苯甲酰基-β-d-葡糖呋喃糖基）尿嘧啶。在其他糖系列中也测试了这种在O-2'处未保护的核苷的新合成方法。在某些情况下，仅获得了1'，2'-顺式核苷，而在其他情况下，仅检测到了1'，2'-顺式核苷的少量收率（3-10％）。α与β之比似乎取决于反应温度。2,4-二甲氧基嘧啶还与糖1,2-亚硫酸盐和4-O-甲基-1-（3,5，
• Nifant'ev, E. E.; Rumyantsev, S. A.; Sisneros, Ks., Journal of general chemistry of the USSR, 1983, vol. 53, # 11, p. 2362 - 2374
  作者：Nifant'ev, E. E.、Rumyantsev, S. A.、Sisneros, Ks.、Koroteev, M. P.、Lutsenko, A. I.、Kochetkov, N. K.

  DOI：——

  日期：——
• Nifant'ev, E. E.; Rumyantseva, S. A.; Koroteev, M. P., Journal of general chemistry of the USSR, 1982, vol. 52, # 4, p. 819 - 820
  作者：Nifant'ev, E. E.、Rumyantseva, S. A.、Koroteev, M. P.、Sisneros, Ks.、Kochetkov, N. K.

  DOI：——

  日期：——
• <scp>D</scp>-XYLOSE (<scp>D</scp>-GLUCOSE) ISOMERASE (EC 5.3.1.5): OBSERVATIONS AND COMMENTS CONCERNING STRUCTURAL REQUIREMENTS OF SUBSTRATES AS WELL AS MECHANISTIC FEATURES
  作者：Herwig Häusler、Hansjörg Weber、Arnold E. Stütz*

  DOI：10.1081/car-100104860

  日期：2001.4.30

  In the course of investigations into the applicability of xylose isomerase as a reagent for carbohydrate synthesis, some questions raised in context with structural requirements for productive substrates as well as mechanistic considerations have been addressed. Amongst the interesting findings obtained so far is the observation that the enzyme requires two vicinal hydroxyl groups, either at positions C-3 and C-4 or at C-4 and C-5, for productive binding/catalysis. Furthermore, two apparently different reaction pathways occur in parallel when certain aldopentoses as well as selected aldohexoses are offered as substrates, this explaining the recently observed formation of epimeric aldoses together with the expected ketoses observed upon extended reaction times.
• Synthesis of a new chiral oxazolidinone auxiliary based on d-xylose and its application to the Staudinger reaction
  作者：Robert Saul、Jürgen Kopf、Peter Köll

  DOI：10.1016/s0957-4166(99)00506-6

  日期：2000.2

  The synthesis of a new chiral oxazolidinone auxiliary based on d-xylose is described which is employed in diastereoselective Staudinger-type β-lactam syntheses. Using 2-chloro-1-methylpyridinium iodide as the dehydrating reagent, the reaction of auxiliary tethered acetic acid with acyclic or cyclic imines gave the desired β-lactams in good yields with excellent cis- or trans-selectivity depending on

  描述了基于d​​-木糖的新型手性恶唑烷酮助剂的合成，其用于非对映选择性施陶丁格型β-内酰胺合成中。使用2-氯-1-甲基碘化碘作为脱水剂，辅助束缚乙酸与无环或环状亚胺的反应可制得所需的β-内酰胺，产率高，取决于亚胺的几何构型，具有优异的顺式或反式选择性。所得化合物之一的X射线结构测定证实了所有顺式产物的绝对构型。