4-methoxyphenyl 2-O-benzyl-4,6-O-cyclohexylidene-β-D-glucopyranoside | 854735-97-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl 2-O-benzyl-4,6-O-cyclohexylidene-β-D-glucopyranoside
• 英文别名: (4aR,6S,7R,8S,8aS)-6-(4-methoxyphenoxy)-7-phenylmethoxyspiro[4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-2,1'-cyclohexane]-8-ol
• CAS: 854735-97-0
• 化学式: C₂₆H₃₂O₇
• 分子量: 456.536
• InChiKey: HAYDOJQYBIRHMC-QERLCLQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 2-O-benzyl-4,6-O-cyclohexylidene-β-D-glucopyranoside 、 p-tolyl 3,5-O-(tetraisopropylsiloxane-1,3-diyl)-1-thio-2-O-triisopropylsilyl-α-D-arabinofuranoside 在 N-碘代丁二酰亚胺 、 3 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 p-methoxyphenyl 3,5-O-(tetraisopropylsiloxane-1,3-diyl)-2-O-triisopropylsilyl-β-D-arabinofuranosyl-(1->3)-2-O-benzyl-4,6-O-cyclohexylidene-α-D-glucopyranoside 、 p-methoxyphenyl 3,5-O-(tetraisopropylsiloxane-1,3-diyl)-2-O-triisopropylsilyl-α-D-arabinofuranosyl-(1->3)-2-O-benzyl-4,6-O-cyclohexylidene-α-D-glucopyranoside
  参考文献：
  名称：

  Stereoselective Synthesis of a Fragment of Mycobacterial Arabinan

  摘要：

  Strategies for the stereoselective synthesis of mycobacterial arabinan were explored. Arabinofuranosyl donors with various protective groups were screened in terms of suitability for beta-( 1,2- cis)- selective glycosylation. The protective group was found to affect the stereoselectivity of arabinofuranosylation. beta-Selectivity was drastically enhanced by using donors protected with 3,5- TIDPS, possibly due to conformational constraints on the furanose ring. Synthesis of heptaarabinofuranoside was then performed to demonstrate the practicality of this methodology.

  DOI：

  10.1021/ol062198j
• 作为产物：
  描述：

  4-甲氧苯基-2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖苷 在 四丁基氟化铵 作用下， 生成 4-methoxyphenyl 2-O-benzyl-4,6-O-cyclohexylidene-β-D-glucopyranoside
  参考文献：
  名称：

  High throughput screening of O-glycosylation conditions

  摘要：

  We report a novel methodology for rapid and quantitative screening of O-glycosylation reactions of application to the analysis of parallel reaction systems. Our system exploits perdeuterated benzyl (Bn-d(7)) ether, and stereoselectivity and yield are evaluated by H-1 NMR and MALDI-TOF MS, respectively. This paper summarizes over 240 screenings of 1 -> 3 linkage formation between glucose residues targeting the alpha-isomer in high yield. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.066

文献信息

• Synergistic solvent effect in 1,2-cis-glycoside formation
  作者：Akihiro Ishiwata、Yuichi Munemura、Yukishige Ito

  DOI：10.1016/j.tet.2007.10.087

  日期：2008.1

  Construction of three continuous 1,2-cis-alpha-glucosidic linkages was achieved in optimized solvent system. High-throughput optimization was conducted, by using substrates protected by perdeuterated benzyl (Bn-d(7)) groups. It enabled facile evaluation of yield and stereoselectivity with H-1 NMR and MALDI-TOF MS, respectively. We found that CHCl3 and ethereal solvent had a synergetic effect to enhance the a-selectivity. The optimized solvent systems in CHCl3/CPME and CHCl3/Et2O were applied to the linear synthesis of Glc alpha 1-2Glc alpha 1-3Glc alpha l-3Man (GlC(3)Man(1)), which was achieved in 86% overall stereo selectivity. (c) 2007 Elsevier Ltd. All rights reserved.