methyl ((2-(hexan-6-ol))5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate | 178872-63-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl ((2-(hexan-6-ol))5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate
• 英文别名: methyl (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-(6-hydroxyhexoxy)-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 178872-63-4
• 化学式: C₂₆H₄₁NO₁₄
• 分子量: 591.61
• InChiKey: RPPMADPDEDTYNE-RLKHCHHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.08
• 重原子数：
  41.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  199.29
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  methyl ((2-(hexan-6-ol))5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate 在 palladium on activated charcoal 4 A molecular sieve 、 四乙基溴化铵 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 168.0h， 生成 (2R,4S,5R,6R)-5-Acetylamino-4-hydroxy-2-[6-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexyloxy]-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of Sialyl Lewis X Analogues

  摘要：

  Sialyl Lewis X (SLe(x)) analogs 2a and 2b were synthesised, where the N-acetyl-D-glucose and the D-galactose units of SLe(x) 1 were replaced with an alkyl and a heteroalkyl spacer. Sulphate ester 6i was also synthesised from alcohol 6b and chlorosulphonic acid. A novel promoter. silver mercaptoethanesulphonate. was used to synthesise alpha-sialosides 2c, 7b and 7c.

  DOI：

  10.1080/07328309608005661
• 作为产物：
  描述：

  methyl ((2-(hexan-6-O-tert-butyldiphenylsilane))5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate 在 吡啶 、 甲醇 、 氢氟酸 、 sodium formate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 methyl ((2-(hexan-6-ol))5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate
  参考文献：
  名称：

  Synthesis and biological evaluation of sialyl-oligonucleotide conjugates targeting leukocyte B trans-membranal receptor CD22 as delivery agents for nucleic acid drugs

  摘要：

  Antisense oligonucleotides (ASOs) modified with ligands which target cell surface receptors have the potential to significantly improve potency in the target tissue. This has recently been demonstrated using triantennary N-acetyl D-galactosamine conjugated ASOs. CD22 is a cell surface receptor expressed exclusively on B cells thus presenting an attractive target for B cell specific delivery of drugs. Herein, we reported the synthesis of monovalent and trivalent ASO conjugates with biphenylcarbonyl (BPC) modified sialic acids and their study as ASO delivery agents into B cells. CD22 positive cells exhibited reduced potency when treated with ligand modified ASOs and mechanistic examination suggested reduced uptake into cells potentially as a result of sequestration of ASO by other cell-surface proteins. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.03.047