methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-O-dibenzyloxyphosphoryl-3,5-dideoxy-β-D-glycero-D-galacto-non-2-ulopyranosonate | 144002-22-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-O-dibenzyloxyphosphoryl-3,5-dideoxy-β-D-glycero-D-galacto-non-2-ulopyranosonate
• 英文别名: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-(dibenzylphosphoryl)-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosonate；methyl (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-bis(phenylmethoxy)phosphoryloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 144002-22-2
• 化学式: C₃₄H₄₂NO₁₆P
• 分子量: 751.678
• InChiKey: XLTXOUDQMXSRGJ-BAMRBWCQSA-N

物化性质

• 沸点：
  791.7±60.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  52
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  215
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-O-dibenzyloxyphosphoryl-3,5-dideoxy-β-D-glycero-D-galacto-non-2-ulopyranosonate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 7.0h， 以99%的产率得到methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosonate 2-phosphate
  参考文献：
  名称：

  Sim, Mui Mui; Kondo, Hirosato; Wong, Chi-Huey, Journal of the American Chemical Society, 1993, vol. 115, # 6, p. 2260 - 2267

  摘要：

  DOI：
• 作为产物：
  描述：

  4,7,8,9-四-O-乙酰基-N-乙酰神经氨酸甲酯 在 四氮唑 、 叔丁基过氧化氢 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-O-dibenzyloxyphosphoryl-3,5-dideoxy-β-D-glycero-D-galacto-non-2-ulopyranosonate
  参考文献：
  名称：

  Sim, Mui Mui; Kondo, Hirosato; Wong, Chi-Huey, Journal of the American Chemical Society, 1993, vol. 115, # 6, p. 2260 - 2267

  摘要：

  DOI：

文献信息

• N,N-Diacetylsialyl chloride—a novel readily accessible sialyl donor in reactions with neutral and charged nucleophiles in the absence of a promoter
  作者：Anna V. Orlova、Anna M. Shpirt、Nadezhda Y. Kulikova、Leonid O. Kononov

  DOI：10.1016/j.carres.2010.01.005

  日期：2010.4

  alpha-glycosyl phosphate, beta-glycosyl dibenzyl phosphate, alpha-glycosyl azide, alpha-phenyl thioglycoside and alpha-glycosyl xanthate in 65-82% yields and high stereoselectivity while its reactions with simple alcohols were not stereoselective. The new sialyl donor made possible the first stereoselective synthesis of sialic acid glycosyl phosphate with alpha-configuration and highly efficient synthesis

  首次制备N，N-二乙酰神经氨酸糖基氯，使其与各种亲核试剂反应，得到相应的α-糖基磷酸酯，β-糖基二苄基磷酸酯，α-糖基叠氮化物，α-苯基硫代糖苷和α-糖基黄药酸酯以65-82％的收率和高的立体选择性，而其与简单醇的反应不是立体选择性的。新的唾液酸供体使得首次立体选择性合成具有α-构型的唾液酸糖基磷酸酯和高效合成β-构型的唾液酸糖基磷酸二苄酯成为可能。
• Kondo, Hirosato; Ichikawa, Yoshitaka; Wong, Chi-Huey, Journal of the American Chemical Society, 1992, vol. 114, # 22, p. 8748 - 8750
  作者：Kondo, Hirosato、Ichikawa, Yoshitaka、Wong, Chi-Huey

  DOI：——

  日期：——
• Convenient chemical synthesis of CMP-N-acetylneuraminate (CMP-Neu-5-Ac)
  作者：Thomas J. Martin、Richard R. Schmidt

  DOI：10.1016/s0040-4039(00)60773-6

  日期：1993.3

  Reaction of sialyl phosphites 1 and 2 with dibenzyl phosphate and phenyl phosphate furnished without addition of a catalyst directly the corresponding sialyl phosphates 3 and 4, respectively, in good yields. Similarly, reaction of 1 with acetylated CMP 5 afforded exclusively beta-configurated acetylated CMP-Neu-5-Ac 6; which was readily transformed into natural sialyl donor CMP-Neu-5-Ac (7).
• Conversion of N-acetylneuraminic acid glycosyl chloride into dibenzyl glycosyl phosphate: O-glycosylation in the absence of a promoter
  作者：A. M. Shpirt、L. O. Kononov、V. I. Torgov、V. N. Shibaev

  DOI：10.1023/b:rucb.0000035663.15439.84

  日期：2004.3

  Readily accessible N-acetylneuraminic acid (Neu5Ac) glycosyl chloride, which was regarded to be a poor glycosyl donor, was shown to react with dibenzyl phosphoric acid salts in the absence of glycosylation promoters to give the corresponding beta-Neu5Ac dibenzyl glycosyl phosphate in high yield.