2-amino-3,4-di-O-acetyl-2-deoxy-α-D-fucopyranosyl phosphate | 405218-94-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-3,4-di-O-acetyl-2-deoxy-α-D-fucopyranosyl phosphate
• 英文别名: [(2R,3S,4R,5R,6R)-4-acetyloxy-5-amino-2-methyl-6-phosphonooxyoxan-3-yl] acetate
• CAS: 405218-94-2
• 化学式: C₁₀H₁₈NO₉P
• 分子量: 327.228
• InChiKey: TXVDBJKRRKWXPT-PMZAMSJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.6
• 重原子数：
  21
• 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：
  155
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-amino-3,4-di-O-acetyl-2-deoxy-α-D-fucopyranosyl phosphate 在 三正丁胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 35.25h， 生成 disodium uridine 5'-(2-acetamido-2-deoxy-α-D-fucopyranosyl diphosphate)
  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 palladium dihydroxide N-甲基咪唑 、 2-溴吡啶 、 sodium azide 、 ammonium cerium(IV) nitrate 、 三氟化硼乙醚 、 氢气 、 锌 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 11.0h， 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

文献信息

• ——
  作者：P. A. Illarionov、V. I. Torgov、I. I. Hancock、V. N. Shibaev

  DOI：10.1023/a:1014035613269

  日期：——

  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.