methyl 5-O-benzyl-β-D-xylofuranoside | 79083-36-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-O-benzyl-β-D-xylofuranoside
• 英文别名: (2R,3R,4R,5R)-2-methoxy-5-(phenylmethoxymethyl)oxolane-3,4-diol
• CAS: 79083-36-6
• 化学式: C₁₃H₁₈O₅
• 分子量: 254.283
• InChiKey: PVICVBVWLIVOKF-YVECIDJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  methyl 5-O-benzyl-β-D-xylofuranoside 在 吡啶 、 氨 、 四氯化锡 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 42.25h， 生成 9-(5-O-benzyl-β-D-xylofuranosyl)adenine
  参考文献：
  名称：

  A Novel Route for the Synthesis of Deoxy Fluoro Sugars and Nucleosides

  摘要：

  The reaction of (diethylamino)sulfur trifluoride (DAST) with methyl 5-O-benzoyl-beta-D-xylofuranoside (1) followed by column chromatography afforded the riboside 2 (62%) and the ribo-epoxide 3 (18%) (Scheme 1). Under similar reaction conditions, the alpha-D-anomer 4 gave the riboside 5 and the difluoride 6 in 60 and 9% yield, respectively Treatment of the beta-D-xyloside 10 with DAST gave, after chromatographic purification, the riboside 11 as the principal product (48% 1 Scheme 2). These results suggest that the C(3)-O-SF2NEt2 derivatives were initially formed in the case of the xylosides studied. The distinctive feature of the reaction of DAST with the beta-D-arabinoside 12 consists in the formation of a 3- or 5-benzylideneoxoniumyl-substituted intermediate on one of the consecutive transformations, which finally give rise to the inversion of the configuration at C(3) affording the xylosides 17 (18%) and 18 (55% ): the lyxoside 14 was also isolated from the reaction mixture in a yield of 25% (Scheme 3). In the presence of the non-participating 5-O-trityl group, i.e.,from the reaction products of 21 with DAST. the compounds 23 and 23 were isolated in 16 and 52% yield, respectively (Scheme 4). It may be thus reasonable to conclude that, in the case of the beta-D-arabinosides 12 and 21, the principal route of the reaction is the formation of the intermediate C(2)-O-SF2NEt2 derivative. Unlike the alpha-D-arabinoside 26 was converted to the lyxo-epoxide 25 (53%) and the lyxoside 27 (14%), which implies the intermediate formation of the C(3)-O-SF2NEt2 derivative (Scheme 5).

  DOI：

  10.1002/(sici)1522-2675(19991110)82:11<2052::aid-hlca2052>3.0.co;2-7
• 作为产物：
  描述：

  1,2-O-cyclohexylidene-5-O-tosyl-α-D-xylofuranose 在 硫酸 、 sodium methylate 、 sodium 作用下， 以 甲醇 为溶剂， 反应 27.0h， 生成 methyl 5-O-benzyl-β-D-xylofuranoside
  参考文献：
  名称：

  格氏试剂在碳水化合物合成中的应用。三、甲基呋喃糖苷的单向异构化及其呋喃糖环的开环

  摘要：

  甲基呋喃糖苷衍生物与甲基碘化镁或叔丁基溴化镁的异构化以单向方式发生。例如，当 3β 和叔丁基溴化镁在苯-醚中的混合物加热时，甲基 5-O-苄基-β-D-呋喃核糖苷 (3β) 以 95% 的产率转化为相应的 α-异头物 (3α)在约 75°C 下除去乙醚；逆反应（从3α到（3β）没有进行。3β与甲基碘化镁反应得到开链产物（33%），除3α（30%）外，还测试了20种异头异构体，并对其作用机理进行了研究。在反应过程中也观察到用格氏试剂裂解苄基或三苯甲基保护基团。

  DOI：

  10.1246/bcsj.54.1492

文献信息

• Hydrogenolysis of 3,5-0-benzylidene acetals with the LiAlH4-AlCl3 reagent in methyl d-xylofuranosides
  作者：András Lipták、András Neszmélyi、Pavol Kováč、Ján Hirsch

  DOI：10.1016/s0040-4020(01)88893-1

  日期：1981.1

  The hydrogenolysis of methyl 3,5-0-benzylidene-α- and -β-D-xylofuranoside derivatives with the LiAlH4-AlCl3 reagent gave 5-benzyl ethers as main products. In some cases the attack of the reagent occured at the ring oxygen of the furenoside skeleton to yield 5-0-benzyl-1-0-methylxylitol derivatives. The structure of the synthesized compounds was proved by 13C-NMR spectroscopy. Unambiguous assignment

  用LiAlH 4 -AlCl 3试剂将3，5-0-亚苄基-α-和-β-D-木呋喃糖苷甲基衍生物氢解，得到5-苄基醚作为主要产物。在某些情况下，试剂的攻击发生在呋喃糖苷骨架的环氧上，从而产生5-0-苄基-1-0-甲基木糖醇衍生物。合成的化合物的结构通过13 C-NMR光谱证实。在13 C-NMR光谱中已对许多部分甲基化的甲基α-和β-d-x-呋喃呋喃糖苷衍生物进行了明确的分配。
• Gopishetty, Bhaskar; Zhu, Jinge; Rajan, Rakhi, Journal of the American Chemical Society, 2009, vol. 131, p. 1243 - 1250
  作者：Gopishetty, Bhaskar、Zhu, Jinge、Rajan, Rakhi、Sobczak, Adam J.、Wnuk, Stanislaw F.、et al.

  DOI：——

  日期：——