3-trifluoroacetamidopropyl 3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)-2-O-benzoyl-4,6-di-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside | 1112455-66-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-trifluoroacetamidopropyl 3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)-2-O-benzoyl-4,6-di-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
• 英文别名: N-[3-[(2S,3S,4S,5R,6R)-3-[(2R,3S,4S,5R,6R)-3-[(2R,3S,4S,5R,6R)-3-benzoyloxy-4-[(2R,3S,4R,5R,6R)-3-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-5-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxypropyl]-2,2,2-trifluoroethanimidic acid
• CAS: 1112455-66-9
• 化学式: C₁₁₃H₁₁₈F₃NO₂₃
• 分子量: 1915.17
• InChiKey: ZUXFVHYLMTUEST-AFRDPXLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.7
• 重原子数：
  140
• 可旋转键数：
  51
• 环数：
  16.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  255
• 氢给体数：
  2
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  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 、 3-trifluoroacetamidopropyl 3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)-2-O-benzoyl-4,6-di-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以67%的产率得到3-trifluoroacetamidopropyl 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-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)-2-O-benzoyl-4,6-di-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-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：

  3-trifluoroacetamidopropyl 3,4,6-tri-O-benzyl-2-O-chloroacetyl-α-D-mannopyranosyl-(1->3)-2-O-benzoyl-4,6-di-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 2,4,6-三甲基吡啶 、 硫脲 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 72.0h， 以83%的产率得到3-trifluoroacetamidopropyl 3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)-2-O-benzoyl-4,6-di-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-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

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.