4-Oxo-pentanoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-pent-4-enyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester | 915150-35-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 4-Oxo-pentanoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-pent-4-enyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester
• 英文别名: [(2S,3S,4S,5R,6R)-2-pent-4-enoxy-4,5-bis(phenylmethoxy)-6-[tri(propan-2-yl)silyloxymethyl]oxan-3-yl] 4-oxopentanoate
• CAS: 915150-35-5
• 化学式: C₃₉H₅₈O₈Si
• 分子量: 682.97
• InChiKey: SHYXLJAMUBPCPS-PXNOONKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.34
• 重原子数：
  48
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-Oxo-pentanoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-pent-4-enyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester 在 N-溴代丁二酰亚胺(NBS) 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 0.5h， 生成 1-O-[3,4-di-O-benzyl-2-O-levulinoyl-6-O-(triisopropylsilyl)-α-D-mannopyranosyl] trichloroacetimidate
  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：

  1,2-O-(α-methoxybenzylidene)-3,4,6-tri-O-benzoyl-β-D-mannopyranose 在 咪唑 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 sodium hydride 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.25h， 生成 4-Oxo-pentanoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-pent-4-enyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester
  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