methyl 3-O-benzyl-α-D-arabinofuranoside | 440359-25-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-benzyl-α-D-arabinofuranoside
• 英文别名: (2S,3S,4S,5R)-5-(hydroxymethyl)-2-methoxy-4-phenylmethoxyoxolan-3-ol
• CAS: 440359-25-1
• 化学式: C₁₃H₁₈O₅
• 分子量: 254.283
• InChiKey: NBVZHEHFHYANST-XQHKEYJVSA-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 3-O-benzyl-α-D-arabinofuranoside 在 palladium dihydroxide 吡啶 、 咪唑 、 ruthenium trichloride 、 sodium periodate 、 N-溴代丁二酰亚胺(NBS) 、 4 A molecular sieve 、 氢氟酸 、 四丁基氟化铵 、 氢气 、 sodium methylate 、 sodium acetate 、 potassium carbonate 、 对甲苯磺酸 、 barium carbonate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 166.5h， 生成 methyl 2,6-anhydro-3-C-hydroxymethyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Oligofuranosides Containing Conformationally Restricted Residues:  Synthesis and Conformational Analysis

  摘要：

  The synthesis of a panel of arabinofuranosyl oligosaccharide analogues (5-13) in which one ring is locked into either the E-3 or E-O conformation is described. The E-3-locked scaffolds 15 and 16 required for the synthesis of 5-10 were prepared in one step from known 1,5-anhydroalditols. A number of routes were explored for the preparation of the E-O-locked monosaccharide derivative 17 needed for the preparation of 11-13. The successful synthesis of 17 was achieved in 17 steps from D-arabinose. Subsequent analysis of 5-13 by H-1 NMR spectroscopy demonstrated that the locked residue does not exert any detectable influence upon the conformers populated by adjacent conformationally unrestricted furanose rings.

  DOI：

  10.1021/jo011127p
• 作为产物：
  描述：

  苯甲醇钠 、 methyl 2,3-anhydro-α-D-lyxofuranoside 以 苯甲醇 为溶剂， 反应 24.0h， 以80%的产率得到methyl 3-O-benzyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Probing the Effect of Acylation on Arabinofuranose Ring Conformation in Di- and Trisaccharide Fragments of Mycobacterial Arabinogalactan

  摘要：

  A major component of the cell wall of mycobacteria is the mycolyl-arabinogalactan (mAG) complex. The arabinose and galactose residues in mAG are found solely in the furanose form, and it has been suggested that the flexibility of these five-membered rings allows for the tight packing of mycolic acids. In order to probe the "flexible scaffold hypothesis", we designed and synthesized glycolipids 3-6 and 8-11 as simple models of the terminal portion of mAG. A set of donors and acceptors were explored for preparing the key beta-(1 -> 2) linkage in 2-6, and the best selectivity and yield can be obtained by using the electron-rich thioglycoside donor 14 and the O-5 p-methoxybenzyl-protected acceptor 17. Both alpha-linkages in the trisaccharides 7-11 were formed in a one-pot reaction. The conformations of compounds 2-11 were studied using solution-state NMR spectroscopy, but little change was observed in the coupling constants for the ring protons between 2 and 3-6 or between 7 and 8-11. However, the rotamer populations about the C-4-C-5 bond for the beta-linked ring in disaccharide 2 did change upon acylation at O-5.

  DOI：

  10.1021/jo100575a

文献信息

• A Siloxane-Bridged Glycosyl Donor Enables Highly Stereoselective β-Xylulofuranosylation
  作者：Bo-Shun Huang、Todd L. Lowary

  DOI：10.1021/acs.joc.0c01008

  日期：2020.12.18

  We report a siloxane-protected donor (7) for the highly stereoselective formation of β-(2,3-cis)-xylulofuranosyl bonds. Glycosylation reactions with 7 gave >80% yields, and only β-xylulofuranosides were isolated in all cases. The utility of 7 for the synthesis of complex glycans was shown by its successful application to the preparation of the repeating unit from the lipopolysaccharide O-antigen of

  我们报告了硅氧烷保护的供体（7）的β-（2,3-顺式）-xylulofuranosyl键的高度立体选择性形成。7种糖基化反应的收率> 80％，在所有情况下仅分离出β-木氟呋喃糖苷。的效用7为复合聚糖的合成所示的成功应用从脂多糖O-抗原制备的重复单元的至小肠结肠炎耶尔森菌血清型○：5 / O：5,27。该结构是具有两个β-木酮呋喃糖残基的五糖。使用7，同时引入了具有出色的立体声控制功能。
• Oligofuranosides Containing Conformationally Restricted Residues:  Synthesis and Conformational Analysis
  作者：Justin B. Houseknecht、Todd L. Lowary

  DOI：10.1021/jo011127p

  日期：2002.6.1

  The synthesis of a panel of arabinofuranosyl oligosaccharide analogues (5-13) in which one ring is locked into either the E-3 or E-O conformation is described. The E-3-locked scaffolds 15 and 16 required for the synthesis of 5-10 were prepared in one step from known 1,5-anhydroalditols. A number of routes were explored for the preparation of the E-O-locked monosaccharide derivative 17 needed for the preparation of 11-13. The successful synthesis of 17 was achieved in 17 steps from D-arabinose. Subsequent analysis of 5-13 by H-1 NMR spectroscopy demonstrated that the locked residue does not exert any detectable influence upon the conformers populated by adjacent conformationally unrestricted furanose rings.
• Probing the Effect of Acylation on Arabinofuranose Ring Conformation in Di- and Trisaccharide Fragments of Mycobacterial Arabinogalactan
  作者：Chunjuan Liu、Michele R. Richards、Todd L. Lowary

  DOI：10.1021/jo100575a

  日期：2010.8.6

  A major component of the cell wall of mycobacteria is the mycolyl-arabinogalactan (mAG) complex. The arabinose and galactose residues in mAG are found solely in the furanose form, and it has been suggested that the flexibility of these five-membered rings allows for the tight packing of mycolic acids. In order to probe the "flexible scaffold hypothesis", we designed and synthesized glycolipids 3-6 and 8-11 as simple models of the terminal portion of mAG. A set of donors and acceptors were explored for preparing the key beta-(1 -> 2) linkage in 2-6, and the best selectivity and yield can be obtained by using the electron-rich thioglycoside donor 14 and the O-5 p-methoxybenzyl-protected acceptor 17. Both alpha-linkages in the trisaccharides 7-11 were formed in a one-pot reaction. The conformations of compounds 2-11 were studied using solution-state NMR spectroscopy, but little change was observed in the coupling constants for the ring protons between 2 and 3-6 or between 7 and 8-11. However, the rotamer populations about the C-4-C-5 bond for the beta-linked ring in disaccharide 2 did change upon acylation at O-5.