4-methoxyphenyl 2-O-(benzyl-d7)-4,6-O-cyclohexylidene-β-D-glucopyranoside | 854735-93-6

• 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-d7)-4,6-O-cyclohexylidene-β-D-glucopyranoside
• 英文别名: (4aR,6S,7R,8S,8aS)-7-[dideuterio-(2,3,4,5,6-pentadeuteriophenyl)methoxy]-6-(4-methoxyphenoxy)spiro[4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-2,1'-cyclohexane]-8-ol
• CAS: 854735-93-6
• 化学式: C₂₆H₃₂O₇
• 分子量: 463.48
• InChiKey: HAYDOJQYBIRHMC-IHSCPGPOSA-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-d7)-4,6-O-cyclohexylidene-β-D-glucopyranoside 、 methyl 4,6-O-cyclohexylidene-2-O-2-naphthylmethyl-1-thio-3-O-triisopropylsilyl-β-D-glucopyranoside 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,2-二氯乙烷 为溶剂， 以84%的产率得到2-naphthaldehyde (4-methoxyphenyl 2-O-[D7]benzyl-4,6-O-cyclohexylidene-β-D-glucopyranosid-3-yl) (methyl 3-O-triisopropylsilyl-4,6-O-cyclohexylidene-1-thio-β-D-glucopyranosid-2-yl) acetal
  参考文献：
  名称：

  NAP 醚介导的分子内糖基传递：1,2-顺式-糖基化的统一策略

  摘要：

  已经开发了一种通过萘甲基 (NAP) 醚介导的分子内苷元衍生 (IAD) 立体选择性构建 1,2-顺式糖苷的方法。通过 NAP-IAD 实现了各种 1,2-顺式连接的立体特异性构建，如β-吡喃甘露糖苷、β-阿拉伯呋喃糖苷和α-吡喃葡萄糖苷。该方法成功应用于合成十四糖Glc 3 Man 9 GlcNAc 2 的非还原末端结构Glca(1→2)-Glcα(1→3)-Glcα(1→3)Man (Glc 3 Man 1 ) ，所有 N 连接聚糖的常见前体。

  DOI：

  10.1002/ejoc.200800249
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 生成 4-methoxyphenyl 2-O-(benzyl-d7)-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.