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.
• Design, synthesis and activity of thio-linked arabinofuranosyl disaccharides against mycobacterial tuberculosis (MTB) and Mycobacterium avium complex (MAC)
  作者：Naveen K. Khare、Franco J. Duarte、Robert C. Reynolds、Joseph A. Maddry

  DOI：10.3998/ark.5550190.0014.222

  日期：——

  We report the chemical synthesis of a series of disaccharides of arabinofuranose with a glycosidic sulfur linker as mimics of the acceptor for arabinofuranosyltransferases with and without using any activator to avoid any complex reactions. These analogs were tested for in vitro activity against MTB strain H37Ra and 3 MAC clinical isolates. MICs were determined using a colorimetric microdilution broth

  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。
• Stereocontrolled Synthesis of 2,3-Anhydro-β-<scp>d</scp>-lyxofuranosyl Glycosides
  作者：Rajendrakumar Reddy Gadikota、Christopher S. Callam、Todd L. Lowary

  DOI：10.1021/ol007008y

  日期：2001.2.1

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