p-tolyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside | 905266-84-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: p-tolyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• 英文别名: 2-[(2R,4aR,6S,7R,8R,8aR)-8-[tert-butyl(dimethyl)silyl]oxy-6-(4-methylphenyl)sulfanyl-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]isoindole-1,3-dione
• CAS: 905266-84-4
• 化学式: C₃₄H₃₉NO₆SSi
• 分子量: 617.838
• InChiKey: DCFQNDXTNQSYMD-ZGEIMPGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.98
• 重原子数：
  43
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  99.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-tolyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 硼烷四氢呋喃络合物 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以0.39 g的产率得到p-tolyl 2-deoxy-2-N-phthalimido-3-O-tert-butyldimethylsilyl-4-O-benzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Iterative one-pot syntheses of chitotetroses

  摘要：

  Rapid syntheses of chitotetrose derivatives were achieved in good yields using the newly developed reactivity independent iterative one-pot strategy. The protective groups on donors and acceptors were independently evaluated allowing matching of the two partners in glycosylation. No anomeric reactivity adjustments or intermediate purification were necessary thus significantly improving the overall synthetic efficiency. Only near stoichiometric amounts of building blocks were required for the assembly of target molecules further highlighting the potential of the iterative one-pot method in complex oligosaccharide synthesis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.01.007
• 作为产物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 、 p-methylphenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 2,6-二甲基吡啶 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以85%的产率得到p-tolyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Iterative one-pot syntheses of chitotetroses

  摘要：

  Rapid syntheses of chitotetrose derivatives were achieved in good yields using the newly developed reactivity independent iterative one-pot strategy. The protective groups on donors and acceptors were independently evaluated allowing matching of the two partners in glycosylation. No anomeric reactivity adjustments or intermediate purification were necessary thus significantly improving the overall synthetic efficiency. Only near stoichiometric amounts of building blocks were required for the assembly of target molecules further highlighting the potential of the iterative one-pot method in complex oligosaccharide synthesis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.01.007

文献信息

• Iterative one-pot syntheses of chitotetroses
  作者：Lijun Huang、Zhen Wang、Xiaoning Li、Xin-shan Ye、Xuefei Huang

  DOI：10.1016/j.carres.2006.01.007

  日期：2006.7

  Rapid syntheses of chitotetrose derivatives were achieved in good yields using the newly developed reactivity independent iterative one-pot strategy. The protective groups on donors and acceptors were independently evaluated allowing matching of the two partners in glycosylation. No anomeric reactivity adjustments or intermediate purification were necessary thus significantly improving the overall synthetic efficiency. Only near stoichiometric amounts of building blocks were required for the assembly of target molecules further highlighting the potential of the iterative one-pot method in complex oligosaccharide synthesis. (c) 2006 Elsevier Ltd. All rights reserved.