2-azido-3,4-di-O-acetyl-2-deoxy-α-D-fucopyranosyl nitrate | 226570-50-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azido-3,4-di-O-acetyl-2-deoxy-α-D-fucopyranosyl nitrate
• 英文别名: 2-azido-3,4-di-O-acetyl-2,6-dideoxy-alpha-d-galactopyranosyl nitrate；[(2R,3S,4R,5R,6R)-4-acetyloxy-5-azido-2-methyl-6-nitrooxyoxan-3-yl] acetate
• CAS: 226570-50-9
• 化学式: C₁₀H₁₄N₄O₈
• 分子量: 318.243
• InChiKey: BHDHWVFRBCKVRT-PMZAMSJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-azido-3,4-di-O-acetyl-2-deoxy-α-D-fucopyranosyl nitrate 在 palladium dihydroxide 2-溴吡啶 、 三氟化硼乙醚 、 氢气 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 2-amino-3,4-di-O-acetyl-2-deoxy-α-D-fucopyranosyl phosphate
  参考文献：
  名称：

  摘要：

  In connection with studies on the biosynthesis of capsular polysaccharides from Staphylococcus aureus, a new synthesis of uridine 5'-(2-acetamido-2,6-dideoxy-alpha-D-galactopyranosyl diphosphate) (uridine 5'-diphospho-N-acetyl-alpha-D-fucosamine) using 2-azido-3,4-di-O-acetyl-2,6-dideoxy-alpha-D-galactopyranosyl nitrate as the key intermediate was carried out. The reaction of this product with cesium dibenzyl phosphate smoothly affords the corresponding beta-glycosyl dibenzyl phosphate, which undergoes anomerization on treatment with BF(3).Et(2)O and 2-bromopyridine to give alpha-glycosyl dibenzyl phosphate in high yield. This product was then transformed into 2-amino-3,4-di-O-acetyl-2,6-dideoxy-alpha-D-galactopyranosyl phosphate, subsequently converted into 2-acetamido-2,6-dideoxy-alpha-D-galactopyranosyl phosphate and the target nucleoside diphosphate sugar.

  DOI：

  10.1023/a:1014035613269
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-D-fucopyranosyl bromide 在 N-甲基咪唑 、 sodium azide 、 ammonium cerium(IV) nitrate 、 锌 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 4.0h， 生成 2-azido-3,4-di-O-acetyl-2-deoxy-α-D-fucopyranosyl nitrate
  参考文献：
  名称：

  摘要：

  In connection with studies on the biosynthesis of capsular polysaccharides from Staphylococcus aureus, a new synthesis of uridine 5'-(2-acetamido-2,6-dideoxy-alpha-D-galactopyranosyl diphosphate) (uridine 5'-diphospho-N-acetyl-alpha-D-fucosamine) using 2-azido-3,4-di-O-acetyl-2,6-dideoxy-alpha-D-galactopyranosyl nitrate as the key intermediate was carried out. The reaction of this product with cesium dibenzyl phosphate smoothly affords the corresponding beta-glycosyl dibenzyl phosphate, which undergoes anomerization on treatment with BF(3).Et(2)O and 2-bromopyridine to give alpha-glycosyl dibenzyl phosphate in high yield. This product was then transformed into 2-amino-3,4-di-O-acetyl-2,6-dideoxy-alpha-D-galactopyranosyl phosphate, subsequently converted into 2-acetamido-2,6-dideoxy-alpha-D-galactopyranosyl phosphate and the target nucleoside diphosphate sugar.

  DOI：

  10.1023/a:1014035613269

文献信息

• Synthesis of glycosyl phosphates from acetylated glycosyl nitrates
  作者：Petr A. Illarionov、Vladimir I. Torgov、Ian C. Hancock、Vladimir N. Shibaev

  DOI：10.1016/s0040-4039(99)00698-x

  日期：1999.5

  Acetylated α-glycosyl nitrates were efficiently converted under mild conditions into protected β-glycosyl phosphates by treatment with cesium dibenzyl phosphate or into thermodynamically more stable α-glycosyl phosphate derivatives upon interaction with cesium diphenyl phosphate. These reactions were found to be applicable both to 2-azido-2,6-dideoxy- and 2-azido-2-deoxygalactopyranosyl nitrates as

  通过用磷酸二苄基铯处理，乙酰化的α-糖基硝酸酯在温和的条件下可以有效地转化为受保护的β-糖基磷酸酯，或者在与磷酸二苯酯铯相互作用时转化为热力学上更稳定的α-糖基磷酸酯衍生物。发现这些反应适用于2-叠氮基2，6-二脱氧-和2-叠氮基2-脱氧半乳糖吡喃糖基硝酸盐以及6-脱氧半乳糖吡喃糖基和半乳糖吡喃糖基的衍生物。