allyl 6-O-(L-glycero-α-D-manno-heptopyranosyl)-α-D-glucopyranoside | 155786-49-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 6-O-(L-glycero-α-D-manno-heptopyranosyl)-α-D-glucopyranoside
• 英文别名: allyl 6-O-(L-glycero-α-D-manno-heptopyanosyl)-α-D-glucopyranoside；LDManHep(a1-6)Glc(a)-O-allyl；(2R,3S,4S,5R,6S)-2-[[(2S,3S,4S,5S,6R)-6-[(1S)-1,2-dihydroxyethyl]-3,4,5-trihydroxyoxan-2-yl]oxymethyl]-6-prop-2-enoxyoxane-3,4,5-triol
• CAS: 155786-49-5
• 化学式: C₁₆H₂₈O₁₂
• 分子量: 412.391
• InChiKey: SVPXVWLEMOZADQ-ZIFVXVTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  199
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 allyl 6-O-(L-glycero-α-D-manno-heptopyranosyl)-α-D-glucopyranoside 以 吡啶 为溶剂， 反应 3.0h， 生成
  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：

  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

文献信息

• HEPTOSE DERIVATIVES FOR USE IN THE TREATMENT OF BACTERIAL INFECTIONS
  申请人：Gerusz Vincent

  公开号：US20140024576A1

  公开（公告）日：2014-01-23

  Compounds having the general formula (I) pharmaceutical compositions containing them for use in inhibiting bacterial heptose biosynthesis and thereby lowering or suppressing bacterial virulence.

  具有通式(I)的化合物，以及含有它们的制药组合物，可用于抑制细菌七糖生物合成，从而降低或抑制细菌的毒力。
• Synthesis of linear oligosaccharides: l-glycero-α-d-manno-heptopyranosyl derivatives of allyl α-glycosides of d-glucose, kojibiose, and 3-O-α-kojibiosyl-d-glucose, substrates for synthetic antigens
  作者：Sergey A. Nepogod'ev、Leon V. Backinowski、Barbara Grzeszczyk、Aleksander Zamojski

  DOI：10.1016/0008-6215(94)84242-6

  日期：1994.2

  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.
• 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
  作者：Konstantin V Antonov、Leon V Backinowsky、Barbara Grzeszczyk、Lore Brade、Otto Holst、Aleksander Zamojski

  DOI：10.1016/s0008-6215(98)00292-4

  日期：1998.12

  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.