4,6-di-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl trichloroacetimidate | 1112455-56-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,6-di-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl trichloroacetimidate
• 英文别名: Bn(-2)[Bn(-3)][Bz(-4)][Bz(-6)]Man(b1-2)[Bn(-3)][Bn(-4)][Bn(-6)]Man(a)-O-C(NH)CCl3；[(2R,3R,4S,5S,6S)-3-benzoyloxy-6-[(2R,3S,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl]oxy-4,5-bis(phenylmethoxy)oxan-2-yl]methyl benzoate
• CAS: 1112455-56-7
• 化学式: C₆₃H₆₀Cl₃NO₁₃
• 分子量: 1145.53
• InChiKey: PRCZTKVATXLQSS-FGZPMKFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  80
• 可旋转键数：
  27
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  160
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  ethyl 4,6-di-O-benzyl-2-O-benzoyl-1-thio-α-D-mannopyranoside 、 4,6-di-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以45%的产率得到ethyl 4,6-di-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)-2-O-benzoyl-4,6-di-O-benzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of a heptasaccharide fragment of the mannan from Candida guilliermondii cell wall and its conjugate with BSA

  摘要：

  The 3-aminopropyl glycoside of a heptasaccharide fragment of the cell wall mannan from Candida guilliermondii 18, which corresponds to the antigenic Factor 9, has been synthesized by a convergent approach based on glycosylation of a tetrasaccharide acceptor with a trisaccharide donor as the key step to give a protected heptasaccharide 17. Subsequent two-step deprotection of 17 afforded the heptamannoside 18, which was then Conjugated with BSA using the squarate procedure. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.09.016
• 作为产物：
  描述：

  4,6-di-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-D-mannopyranose 、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以99%的产率得到4,6-di-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of a heptasaccharide fragment of the mannan from Candida guilliermondii cell wall and its conjugate with BSA

  摘要：

  The 3-aminopropyl glycoside of a heptasaccharide fragment of the cell wall mannan from Candida guilliermondii 18, which corresponds to the antigenic Factor 9, has been synthesized by a convergent approach based on glycosylation of a tetrasaccharide acceptor with a trisaccharide donor as the key step to give a protected heptasaccharide 17. Subsequent two-step deprotection of 17 afforded the heptamannoside 18, which was then Conjugated with BSA using the squarate procedure. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.09.016

文献信息

• Synthesis of a heptasaccharide fragment of the mannan from Candida guilliermondii cell wall and its conjugate with BSA
  作者：Alexander A. Karelin、Yury E. Tsvetkov、Lucia Paulovičová、Slavomír Bystrický、Ema Paulovičová、Nikolay E. Nifantiev

  DOI：10.1016/j.carres.2008.09.016

  日期：2009.1

  The 3-aminopropyl glycoside of a heptasaccharide fragment of the cell wall mannan from Candida guilliermondii 18, which corresponds to the antigenic Factor 9, has been synthesized by a convergent approach based on glycosylation of a tetrasaccharide acceptor with a trisaccharide donor as the key step to give a protected heptasaccharide 17. Subsequent two-step deprotection of 17 afforded the heptamannoside 18, which was then Conjugated with BSA using the squarate procedure. (C) 2008 Elsevier Ltd. All rights reserved.