(2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-pent-4-enyloxy-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester | 142301-33-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-pent-4-enyloxy-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-pent-4-enoxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 142301-33-5
• 化学式: C₂₅H₃₇NO₁₃
• 分子量: 559.568
• InChiKey: KFRNVDPLRLLKIR-QULIQSTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  39
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  179
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-pent-4-enyloxy-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 sodium tetrahydroborate 、 cerium(III) chloride 、 二甲基硫 、 sodium methylate 、 caesium carbonate 、 臭氧 作用下， 以 甲醇 、 乙醇 、 叔丁醇 为溶剂， 反应 48.67h， 生成 methyl 5-acetamido-2-<7''-(methyl 6'-deoxy-β-L-galactopyranoside-4'-yl)-6''-hydroxy-hept-4''-en-1''-yl>-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulosonate
  参考文献：
  名称：

  The synthesis of novel mimics of the sialyl Lewis X determinant

  摘要：

  Disaccharide mimics of the sialyl Lewis X (sLe(x)) ligands have been prepared as potential antagonists of binding to the lectin domains-of the E-selectin adhesion molecule. Versatile derivatives of sialic acid provide an entry to a series of simplified linker groups supporting the fucose and sialyl residues. The stereoselectivity of nucleophilic addition to the fucosyl ketone derivative 7 is determined by the conditions employed; basic and Lewis acid conditions give opposite results(1).

  DOI：

  10.1016/s0957-4166(00)86284-9
• 作为产物：
  描述：

  4-戊烯-1-醇 、 N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 在 4 A molecular sieve 、 silver salicylate 作用下， 以80%的产率得到(2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-pent-4-enyloxy-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  The synthesis of novel mimics of the sialyl Lewis X determinant

  摘要：

  Disaccharide mimics of the sialyl Lewis X (sLe(x)) ligands have been prepared as potential antagonists of binding to the lectin domains-of the E-selectin adhesion molecule. Versatile derivatives of sialic acid provide an entry to a series of simplified linker groups supporting the fucose and sialyl residues. The stereoselectivity of nucleophilic addition to the fucosyl ketone derivative 7 is determined by the conditions employed; basic and Lewis acid conditions give opposite results(1).

  DOI：

  10.1016/s0957-4166(00)86284-9

文献信息

• Facile Preparation of Divalent Sialoside Derivatives by Olefin Metathesis Reaction
  作者：Zhonghong Gan、René Roy

  DOI：10.1016/s0040-4020(00)00034-x

  日期：2000.3

  Olefin metathesis catalyzed by RuCl2(CHPh)(PCy3)(2) (1) has been used to synthesize homodimers of O- and S-alkenyl alpha-sialoside derivatives. The reactions afforded reasonable to good yields under mild reaction conditions. Trans-geometrical isomers were preferred in all cases. (C) 2000 Elsevier Science Ltd. All rights reserved.