pent-4-enyl 5-O-(5-O-{2-O-benzoyl-3-O-[2-O-benzoyl-3-O-benzyl-α-D-arabinofuranosyl]-α-D-arabinofuranosyl}-2-O-benzoyl-3-O-benzyl-α-D-arabinofuranosyl)-2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside | 915150-28-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pent-4-enyl 5-O-(5-O-{2-O-benzoyl-3-O-[2-O-benzoyl-3-O-benzyl-α-D-arabinofuranosyl]-α-D-arabinofuranosyl}-2-O-benzoyl-3-O-benzyl-α-D-arabinofuranosyl)-2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside
• 英文别名: [(2R,3S,4R,5R)-2-[(2R,3R,4S,5S)-4-benzoyloxy-5-[[(2R,3R,4S,5S)-4-benzoyloxy-5-[[(2R,3R,4S,5S)-4-benzoyloxy-5-pent-4-enoxy-3-phenylmethoxyoxolan-2-yl]methoxy]-3-phenylmethoxyoxolan-2-yl]methoxy]-2-(hydroxymethyl)oxolan-3-yl]oxy-5-(hydroxymethyl)-4-phenylmethoxyoxolan-3-yl] benzoate
• CAS: 915150-28-6
• 化学式: C₇₄H₇₆O₂₁
• 分子量: 1301.4
• InChiKey: KSVFCTQTDIDSAA-MDWGDFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  95
• 可旋转键数：
  36
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  247
• 氢给体数：
  2
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  1-O-(2-O-benzoyl-3,5-di-O-benzyl-α-D-arabinofuranosyl) trichloroacetimidate 、 pent-4-enyl 5-O-(5-O-{2-O-benzoyl-3-O-[2-O-benzoyl-3-O-benzyl-α-D-arabinofuranosyl]-α-D-arabinofuranosyl}-2-O-benzoyl-3-O-benzyl-α-D-arabinofuranosyl)-2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.58h， 以92%的产率得到[(2S,3S,4R,5R)-2-[[(2R,3R,4S,5R)-4-benzoyloxy-5-[(2R,3R,4S,5S)-4-benzoyloxy-5-[[(2R,3R,4S,5S)-4-benzoyloxy-5-[[(2R,3R,4S,5S)-4-benzoyloxy-5-pent-4-enoxy-3-phenylmethoxyoxolan-2-yl]methoxy]-3-phenylmethoxyoxolan-2-yl]methoxy]-2-[[(2S,3S,4R,5R)-3-benzoyloxy-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-2-yl]oxymethyl]oxolan-3-yl]oxy-3-phenylmethoxyoxolan-2-yl]methoxy]-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-3-yl] benzoate
  参考文献：
  名称：

  Synthesis of a Core Arabinomannan Oligosaccharide of Mycobacterium tuberculosis

  摘要：

  The synthesis of a core arabinomannan (AM) oligosaccharide from Mycobacterium tuberculosis has been achieved using a convergent [6 + 6] glycosylation strategy and a defined set of building blocks. Dodecasaccharide 1, containing the key AM structural features of lipoarabinomannan (LAM), was obtained in excellent yield and selectivity from hexamannan 3 and hexaarabinan 5. This flexible synthetic strategy involves late-stage couplings and modifications, thus providing ready access to several different LAM fragments. The incorporation of a thiol linker at the reducing end of the oligosaccharide allows for the attachment of these compounds to microarrays and protein carriers.

  DOI：

  10.1021/jo061233x
• 作为产物：
  描述：

  pent-4-enyl 5-O-(5-O-{2-O-benzoyl-3-O-[2-O-benzoyl-3-O-benzyl-5-O-(triisopropylsilyl)-α-D-arabinofuranosyl]-5-O-(triisopropylsilyl)-α-D-arabinofuranosyl}-2-O-benzoyl-3-O-benzyl-α-D-arabinofuranosyl)-2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside 在 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 以87%的产率得到pent-4-enyl 5-O-(5-O-{2-O-benzoyl-3-O-[2-O-benzoyl-3-O-benzyl-α-D-arabinofuranosyl]-α-D-arabinofuranosyl}-2-O-benzoyl-3-O-benzyl-α-D-arabinofuranosyl)-2-O-benzoyl-3-O-benzyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of a Core Arabinomannan Oligosaccharide of Mycobacterium tuberculosis

  摘要：

  The synthesis of a core arabinomannan (AM) oligosaccharide from Mycobacterium tuberculosis has been achieved using a convergent [6 + 6] glycosylation strategy and a defined set of building blocks. Dodecasaccharide 1, containing the key AM structural features of lipoarabinomannan (LAM), was obtained in excellent yield and selectivity from hexamannan 3 and hexaarabinan 5. This flexible synthetic strategy involves late-stage couplings and modifications, thus providing ready access to several different LAM fragments. The incorporation of a thiol linker at the reducing end of the oligosaccharide allows for the attachment of these compounds to microarrays and protein carriers.

  DOI：

  10.1021/jo061233x

文献信息

• Synthesis of a Core Arabinomannan Oligosaccharide of <i>Mycobacterium tuberculosis</i>
  作者：Alexandra Hölemann、Bridget L. Stocker、Peter H. Seeberger

  DOI：10.1021/jo061233x

  日期：2006.10.1

  The synthesis of a core arabinomannan (AM) oligosaccharide from Mycobacterium tuberculosis has been achieved using a convergent [6 + 6] glycosylation strategy and a defined set of building blocks. Dodecasaccharide 1, containing the key AM structural features of lipoarabinomannan (LAM), was obtained in excellent yield and selectivity from hexamannan 3 and hexaarabinan 5. This flexible synthetic strategy involves late-stage couplings and modifications, thus providing ready access to several different LAM fragments. The incorporation of a thiol linker at the reducing end of the oligosaccharide allows for the attachment of these compounds to microarrays and protein carriers.