methyl 7-O-L-glycero-α-D-manno-heptopyranosyl-L-glycero-α-D-manno-heptopyranoside | 131289-48-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 7-O-L-glycero-α-D-manno-heptopyranosyl-L-glycero-α-D-manno-heptopyranoside
• 英文别名: methyl L-glycero-α-D-manno-heptopyranosyl-(1->7)-L-glycero-α-D-manno-heptopyranoside；LDManHep(a1-7)a-LDManHep1Me；(2R,3S,4S,5S,6S)-2-[(1S)-1,2-dihydroxyethyl]-6-[(2S)-2-hydroxy-2-[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]ethoxy]oxane-3,4,5-triol
• CAS: 131289-48-0
• 化学式: C₁₅H₂₈O₁₃
• 分子量: 416.38
• InChiKey: SSJCJFBAYWAUIP-NGYLIJNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.9
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  219
• 氢给体数：
  9
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside 在 palladium on activated charcoal 吡啶 、 2,4,6-三甲基吡啶 、 4-二甲氨基吡啶 、 1,1-二溴乙烷 、 4 A molecular sieve 、 氢气 、 双氧水 、 sodium methylate 、 silver trifluoromethanesulfonate 、 碳酸氢钠 、 magnesium 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 25.0 ℃ 、399.99 kPa 条件下， 反应 41.5h， 生成 methyl 7-O-L-glycero-α-D-manno-heptopyranosyl-L-glycero-α-D-manno-heptopyranoside
  参考文献：
  名称：

  Synthesis of methyl 3-O-(α-d-glucopyranosyl)-7-O-(l-glycero-α-d-manno-heptopyranosyl)-l-glycero-α-d-manno- heptopyranoside

  摘要：

  The title trisaccharide glycoside, which is related to part of the core region of the lipopolysaccharide from Salmonella, and the disaccharide glycosides methyl 3-O-alpha-D-glucopyranosyl-L-glycero-alpha-D-manno-heptopyranoside and methyl 7-O-L-glycero-alpha-D-manno-heptopyranosyl-L-glycero-alpha-D-manno- heptopyranoside have been synthesised. Methyl 2,3,4-tri-O-benzyl-L-glycero-alpha-D-manno- heptopyranoside, obtained via a one-carbon elongation at C-6 of methyl 2,3,4-tri-O-benzyl-alpha-D-manno- hexodialdo-1,5-pyranoside, was used as precursor both for the heptosyl donor and acceptor.

  DOI：

  10.1016/0008-6215(90)80133-n

文献信息

• Crystal and molecular structure of methyl l-glycero-α-d-manno-heptopyranoside, and synthesis of 1→7 linked l-glycero-d-manno-heptobiose and its methyl α-glycoside
  作者：Daniel Artner、Christian Stanetty、Kurt Mereiter、Alla Zamyatina、Paul Kosma

  DOI：10.1016/j.carres.2011.05.033

  日期：2011.9

  Graphical abstract

  图形概要
• 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 methyl 3-O-(α-d-glucopyranosyl)-7-O-(l-glycero-α-d-manno-heptopyranosyl)-l-glycero-α-d-manno- heptopyranoside
  作者：Per J. Garegg、Stefan Oscarson、Maria Szo¨nyi

  DOI：10.1016/0008-6215(90)80133-n

  日期：1990.9

  The title trisaccharide glycoside, which is related to part of the core region of the lipopolysaccharide from Salmonella, and the disaccharide glycosides methyl 3-O-alpha-D-glucopyranosyl-L-glycero-alpha-D-manno-heptopyranoside and methyl 7-O-L-glycero-alpha-D-manno-heptopyranosyl-L-glycero-alpha-D-manno- heptopyranoside have been synthesised. Methyl 2,3,4-tri-O-benzyl-L-glycero-alpha-D-manno- heptopyranoside, obtained via a one-carbon elongation at C-6 of methyl 2,3,4-tri-O-benzyl-alpha-D-manno- hexodialdo-1,5-pyranoside, was used as precursor both for the heptosyl donor and acceptor.