pent-4-enyl 2-O-benzoyl-3-O-benzyl-5-O-(triisopropylsilyl)-α-D-arabinofuranoside | 915150-36-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pent-4-enyl 2-O-benzoyl-3-O-benzyl-5-O-(triisopropylsilyl)-α-D-arabinofuranoside
• 英文别名: [(2S,3S,4R,5R)-2-pent-4-enoxy-4-phenylmethoxy-5-[tri(propan-2-yl)silyloxymethyl]oxolan-3-yl] benzoate
• CAS: 915150-36-6
• 化学式: C₃₃H₄₈O₆Si
• 分子量: 568.826
• InChiKey: NOEKAAPBGOAGDX-QFBUMDDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  40
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  pent-4-enyl 2-O-benzoyl-3-O-benzyl-5-O-(triisopropylsilyl)-α-D-arabinofuranoside 在 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 以96%的产率得到pent-4-enyl 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
• 作为产物：
  描述：

  1-O-(2-O-benzoyl-3-O-benzyl-5-O-(triisopropylsilyl)-D-arabinofuranosyl) trichloroacetimidate 、 4-戊烯-1-醇 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以97%的产率得到pent-4-enyl 2-O-benzoyl-3-O-benzyl-5-O-(triisopropylsilyl)-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.