1-O-[3,4-di-O-benzyl-2-O-levulinoyl-6-O-(triisopropylsilyl)-α-D-mannopyranosyl] trichloroacetimidate | 915149-96-1

• 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: 1-O-[3,4-di-O-benzyl-2-O-levulinoyl-6-O-(triisopropylsilyl)-α-D-mannopyranosyl] trichloroacetimidate
• 英文别名: [(2R,3S,4S,5R,6R)-4,5-bis(phenylmethoxy)-2-(2,2,2-trichloroethanimidoyl)oxy-6-[tri(propan-2-yl)silyloxymethyl]oxan-3-yl] 4-oxopentanoate
• CAS: 915149-96-1
• 化学式: C₃₆H₅₀Cl₃NO₈Si
• 分子量: 759.239
• InChiKey: RORKKWKKUZPWHG-QLYCUWNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.72
• 重原子数：
  49
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-O-[3,4-di-O-benzyl-2-O-levulinoyl-6-O-(triisopropylsilyl)-α-D-mannopyranosyl] trichloroacetimidate 、 allyl 2-O-benzoyl-3,4-di-O-benzyl-α-D-mannopyranosyl-(1->6)-2-O-benzoyl-3,4-di-O-benzyl-α-D-mannopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以80%的产率得到allyl 6-O-{6-O-[3,4-di-O-benzyl-2-O-levulinoyl-6-O-(triisopropylsilyl)-α-D-mannopyranosyl]-2-O-benzoyl-3,4-di-O-benzyl-α-D-mannopyranosyl}-2-O-benzoyl-3,4-di-O-benzyl-α-D-mannopyranoside
  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 、 N-溴代丁二酰亚胺(NBS) 、 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 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.75h， 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

文献信息

• Synthesis and immunogenicity of the <i>Mycobacterium tuberculosis</i> arabinomannan–CRM197 conjugate
  作者：Yunsong Chang、Xin Meng、Yaxin Li、Jianmei Liang、Tingshen Li、Demei Meng、Tao Zhu、Peng Yu

  DOI：10.1039/c8md00546j

  日期：——

  T-dependent conjugate vaccine. Preliminary mice immunization studies on the neoglycoconjugate revealed that it could give rise to a strong IgG antibody titer in mice at 4.0 μg dose with an aluminum phosphate adjuvant. AM–CRM197 shows potential as an excellent candidate for a new carbohydrate-based vaccine that would be capable of eliciting a protective immune response against tuberculosis.

  Lipoarabinomannan（LAM）是结核分枝杆菌的主要结构表面成分。这项研究描述了明确定义的脂阿拉伯糖甘露聚糖（LAM）特异性十二糖-蛋白质结合物的合成和免疫学研究。阿拉伯甘露聚糖（AM）十二糖已被有效地合成并与载体蛋白共价缀合，包括交叉反应突变体（CRM197）白喉类毒素和牛血清白蛋白（BSA）用于新型新糖缀合物，从而产生了强效的T依赖性缀合物疫苗。小鼠对新糖缀合物的初步免疫研究表明，使用磷酸铝佐剂可以以4.0μg的剂量在小鼠中产生较强的IgG抗体效价。AM-CRM197有望成为新型碳水化合物疫苗的潜在候选者，该疫苗能够引发针对肺结核的保护性免疫应答。
• 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.