methyl 5-O-benzyl-α-D-arabinofuranoside | 237410-28-5

• 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-α-D-arabinofuranoside
• 英文别名: 5-O-benzyl-2,3-anhydro-α-D-lyxofuranoside；(2S,3S,4S,5R)-2-methoxy-5-(phenylmethoxymethyl)oxolane-3,4-diol
• CAS: 237410-28-5
• 化学式: C₁₃H₁₈O₅
• 分子量: 254.283
• InChiKey: PVICVBVWLIVOKF-NDBYEHHHSA-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-α-D-arabinofuranoside 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯甲醇 为溶剂， 反应 2.5h， 生成 methyl 2-O-(2,3-anhydro-5-O-benzoyl-β-D-lyxofuranosyl)-3,5-di-O-benzyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Stereocontrolled Synthesis of 2,3-Anhydro-β-d-lyxofuranosyl Glycosides

  摘要：

  [GRAPHICS]The stereocontrolled synthesis of 2,3-anhydro-beta -D-lyxofuranosyl glycosides from thioglycoside 2 and glycosyl sulfoxide 3 is reported.

  DOI：

  10.1021/ol007008y
• 作为产物：
  描述：

  methyl 2,3-di-O-(4-methoxybenzyl)-5-O-(tert-butyldiphenylsilyl)-α-D-arabinofuranoside 在 ammonium cerium (IV) nitrate 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 25.5h， 生成 methyl 5-O-benzyl-α-D-arabinofuranoside
  参考文献：
  名称：

  硫连接的阿拉伯呋喃糖基二糖的设计、合成和活性对结核分枝杆菌 (MTB) 和鸟分枝杆菌复合体 (MAC)

  摘要：

  我们报告了一系列带有糖苷硫接头的阿拉伯呋喃糖二糖的化学合成，作为阿拉伯呋喃基转移酶受体的模拟物，使用或不使用任何激活剂以避免任何复杂反应。测试了这些类似物对 MTB 菌株 H37Ra 和 3 个 MAC 临床分离株的体外活性。MIC 使用比色微量稀释肉汤测定来确定。杀菌活性是用 7 天的杀菌曲线研究的。在 Mono Mac 6 (MM6) 人单核细胞系中测定了针对 MTB H37Ra 的细胞内活性。

  DOI：

  10.3998/ark.5550190.0014.222

文献信息

• A Novel Route for the Synthesis of Deoxy Fluoro Sugars and Nucleosides
  作者：Igor A. Mikhailopulo、Grigorii G. Sivets

  DOI：10.1002/(sici)1522-2675(19991110)82:11<2052::aid-hlca2052>3.0.co;2-7

  日期：1999.11.10

  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).
• A Novel Route for the Synthesis of Fluorodeoxy Sugars and Nucleosides
  作者：Igor A. Mikhailopulo、Grigorii G. Sivets、Natalia B. Khripach

  DOI：10.1080/15257779908041542

  日期：1999.4

  Ring-fluorination of alpha- and beta-D-pentofuranosides containing free secondary hydroxyl groups by (diethylamino)sulfur trifluoride (DAST) was studied.