benzyl (3-O-tert-butyldiphenylsilyl-4,6-O-cyclohexylidene-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 877669-88-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl (3-O-tert-butyldiphenylsilyl-4,6-O-cyclohexylidene-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• 英文别名: 2-[(2R,3R,4R,5S,6R)-5-[(4aR,6S,7S,8R,8aR)-8-[tert-butyl(diphenyl)silyl]oxy-7-hydroxyspiro[4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-2,1'-cyclohexane]-6-yl]oxy-2,4-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]isoindole-1,3-dione
• CAS: 877669-88-0
• 化学式: C₆₃H₆₉NO₁₂Si
• 分子量: 1060.33
• InChiKey: HKWQZWYFPYQYCJ-PCLYFXIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.89
• 重原子数：
  77
• 可旋转键数：
  18
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  141
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  benzyl (3-O-tert-butyldiphenylsilyl-4,6-O-cyclohexylidene-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 、 2,3,4-tri-O-acetyl-D-xylopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以67%的产率得到benzyl (2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1->2)-(3-O-tert-butyldiphenylsilyl-4,6-O-cyclohexylidene-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of complex-type glycans derived from parasitic helminths

  摘要：

  Chemical syntheses of complex-type glycans derived from the eggs of parasitic helminths, Schistosoma mansoni and Schistosoma japonicum were achieved. In addition, their analogs, which lack xylose and/or fucose residue(s), are 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) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.12.022
• 作为产物：
  描述：

  methyl 4,6-O-cyclohexylidene-2-O-p-methoxybenzyl-3-O-tert-butyldiphenylsilyl-1-thio-α-D-mannopyranoside 在 2,6-二叔丁基-4-甲基吡啶 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三氟甲烷磺酸甲酯 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 25.5h， 生成 benzyl (3-O-tert-butyldiphenylsilyl-4,6-O-cyclohexylidene-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-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.