allyl 2,3,4-tri-O-acetyl-6-O-[2,3,4,6-tetra-O-acetyl-7-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-L-glycero-α-D-manno-heptopyranosyl]-α-D-glucopyranoside | 223436-29-1

• 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-acetyl-6-O-[2,3,4,6-tetra-O-acetyl-7-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-L-glycero-α-D-manno-heptopyranosyl]-α-D-glucopyranoside
• CAS: 223436-29-1
• 化学式: C₄₄H₆₁NO₂₇
• 分子量: 1035.96
• InChiKey: VMNLUJVNLKSHQR-PCWVXJEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.15
• 重原子数：
  72.0
• 可旋转键数：
  22.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  347.48
• 氢给体数：
  1.0
• 氢受体数：
  27.0

反应信息

• 作为反应物：
  描述：

  allyl 2,3,4-tri-O-acetyl-6-O-[2,3,4,6-tetra-O-acetyl-7-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-L-glycero-α-D-manno-heptopyranosyl]-α-D-glucopyranoside 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以98%的产率得到allyl 6-O-[7-O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-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：

  乙酸酐 、 、 [(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-acetyloxy-2-[(2R,3R,4R,5S,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-(1,3-dioxoisoindol-2-yl)oxan-2-yl]oxyethyl]oxan-2-yl]oxymethyl]oxan-3-yl] benzoate 在 乙二胺 、 4-二甲氨基吡啶 作用下， 以 正丁醇 、 吡啶 为溶剂， 反应 24.0h， 以89%的产率得到allyl 2,3,4-tri-O-acetyl-6-O-[2,3,4,6-tetra-O-acetyl-7-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-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