allyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranosyl)-α-D-glucopyranoside | 155786-55-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranosyl)-α-D-glucopyranoside
• 英文别名: LDManHep2Ac3Ac4Ac6Ac7Ac(a1-6)[Bz(-2)][Bz(-3)][Bz(-4)]Glc(a)-O-allyl；[(2R,3R,4S,5R,6S)-4,5-dibenzoyloxy-6-prop-2-enoxy-2-[[(2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[(1S)-1,2-diacetyloxyethyl]oxan-2-yl]oxymethyl]oxan-3-yl] benzoate
• CAS: 155786-55-3
• 化学式: C₄₇H₅₀O₂₀
• 分子量: 934.902
• InChiKey: JNIWQABTPRKTQW-XQFTURDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  67
• 可旋转键数：
  27
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  247
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  allyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranosyl)-α-D-glucopyranoside 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 96.0h， 生成 allyl 6-O-(L-glycero-α-D-manno-heptopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and serological characterization of l-glycero-α-d-manno-heptopyranose-containing di- and tri-saccharides of the non-reducing terminus of the Escherichia coli K-12 LPS core oligosaccharide

  摘要：

  Synthesis of the title trisaccharide was accomplished by sugar chain extension starting from the non-reducing terminus: coupling of GlcpNAc with LD-Hepp, then adding Glcp-OAll. An alternative route started from the reducing end: coupling of LD-Hepp with Glcp-OAll, then addition of GlcpNAc. In the synthesis of the title disaccharide a modification of the first approach was employed. The allyl glycosides were coupled with cysteamine, activated with thiophosgene and conjugated to bovine serum albumin (BSA). The neoglycoconjugates obtained were used in immunochemical studies of monoclonal and polyclonal antibodies directed against Escherichia coli K-12 lipopolysaccharide. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00292-4
• 作为产物：
  描述：

  烯丙基-alpha-D-吡喃葡萄糖苷 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 allyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  线性寡糖的合成：D-葡萄糖，曲霉二糖和3-O-α-曲霉生物基-D-葡萄糖的烯丙基α-糖苷的L-甘油-α-D-甘露聚糖-戊糖基衍生物，是合成抗原的底物。

  摘要：

  Synthesis of the title oligosaccharides was performed with the use of peracetylated L-glycero-beta-D-manno-heptosyl trichloroacetimidate as the heptosyl donor and (oligo)glucosyl accepters bearing acyl and acetal protecting groups.

  DOI：

  10.1016/0008-6215(94)84242-6