benzyl 2-deoxy-3-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside | 877669-94-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-deoxy-3-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside
• 英文别名: 2-[(2R,3R,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-4-[(4-methoxyphenyl)methoxy]-2-phenylmethoxyoxan-3-yl]isoindole-1,3-dione
• CAS: 877669-94-8
• 化学式: C₂₉H₂₉NO₈
• 分子量: 519.551
• InChiKey: HDFLYALCSOWTNC-ZOLYYXPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl 2-deoxy-3-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside 、 Acetic acid (2S,3R,4R,5S,6R)-3-acetoxy-5-benzyloxy-2-methyl-6-methylsulfanyl-tetrahydro-pyran-4-yl ester 在 2,6-di-tert-butyl-4-methoxypyridine 、 三氟甲烷磺酸甲酯 作用下， 以 various solvent(s) 为溶剂， 反应 22.0h， 以66%的产率得到Acetic acid (2S,3R,4R,5S,6R)-3-acetoxy-5-benzyloxy-6-[(2R,3S,4R,5R,6R)-6-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethoxy]-2-methyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis of complex-type glycans derived from parasitic helminths

  摘要：

  Chemical synthesis of complex-type glycans 1 and 2 derived from eggs of parasitic helminths, Schistosoma mansoni and Schistosoma japonicum, is described. These branched sugar chains were synthesized regio- and stereo selectively by using beta-mannosylation, desilylation under high pressure, and glycosylation in frozen solvent as key transformations. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.100
• 作为产物：
  描述：

  benzyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 对甲苯磺酸 、 lanthanum(lll) triflate 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 31.0h， 生成 benzyl 2-deoxy-3-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of complex-type glycans derived from parasitic helminths

  摘要：

  Chemical synthesis of complex-type glycans 1 and 2 derived from eggs of parasitic helminths, Schistosoma mansoni and Schistosoma japonicum, is described. These branched sugar chains were synthesized regio- and stereo selectively by using beta-mannosylation, desilylation under high pressure, and glycosylation in frozen solvent as key transformations. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.100

文献信息

• Synthesis of complex-type glycans derived from parasitic helminths
  作者：Jun Nakano、Hiromichi Ohta、Yukishige Ito

  DOI：10.1016/j.bmcl.2005.10.100

  日期：2006.2

  Chemical synthesis of complex-type glycans 1 and 2 derived from eggs of parasitic helminths, Schistosoma mansoni and Schistosoma japonicum, is described. These branched sugar chains were synthesized regio- and stereo selectively by using beta-mannosylation, desilylation under high pressure, and glycosylation in frozen solvent as key transformations. (c) 2005 Elsevier Ltd. All rights reserved.