cesium dibenzyl phosphate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: cesium dibenzyl phosphate
• 英文别名: cesium;dibenzyl phosphate
• 化学式: C₁₄H₁₄O₄P*Cs
• 分子量: 410.142
• InChiKey: PAXWAJHLBARVGG-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.11
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl nitrate 、 cesium dibenzyl phosphate 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以75%的产率得到dibenzyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) phosphate
  参考文献：
  名称：

  由乙酰化的糖基硝酸酯合成糖基磷酸酯

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(99)00698-x

文献信息

• The synthesis ofN-acetyl-β-l-fucosamine-1-phosphate and uridine 5′-diphospho-N-acetyl-β-l-fucosamine
  作者：P. A. Illarionov、V. I. Torgov、I. Hancock、V. N. Shibaev

  DOI：10.1007/bf02494930

  日期：2000.11

  Uridine 5′-(2-acetamido-2,6-dideoxy-β-l-galactopyranosyl) diphosphate (uridine 5′-diphospho-N-acetyl-β-l-fucosamine) was synthesized. The key intermediate, 3,4-di-O-acetyl-2-azido-2,6-dideoxy-β-l-galactopyranosyl dibenzyl phosphate, was prepared by a previously unknown reaction of cesium dibenzyl phosphate with the corresponding α-glycosyl nitrate and was then converted into theN-acetylated glycosyl

  合成了尿苷 5'-（2-乙酰氨基-2,6-二脱氧-β-1-吡喃半乳糖基）二磷酸（尿苷 5'-二磷酸-N-乙酰基-β-1-岩藻糖胺）。关键中间体 3,4-di-O-acetyl-2-azido-2,6-dideoxy-β-l-galactopyranosyl dibenzyl phosphate 是通过先前未知的磷酸二苄基铯与相应的 α-糖基硝酸酯反应制备的然后通过温和的N-乙酰化和O-脱乙酰作用，通过3,4-二-O-乙酰-2-氨基-2,6-二脱氧-β-1-吡喃半乳糖基磷酸酯转化为N-乙酰化磷酸糖和核苷二磷酸糖合成步骤。
• 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。
• ——
  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.
• The use of cesium dibenzyl and diphenyl phosphates for stereoselective synthesis of glycosyl phosphate derivatives
  作者：P. A. Illarionov、V. I. Torgov、V. N. Shibaev

  DOI：10.1007/bf02494931

  日期：2000.11

  Peracetates of β-glycosyl dibenzyl phosphates are formed efficiently in the reaction of cesium dibenzyl phosphate with peracetyl-α-glycosyl nitrates derived froml-fucopyranose,d-galactopyranose, and 2-azido-2-deoxy-d-galactopyranose or with tri-O-acetyl-α-l-fucopyranosyl bromide. On the contrary, the reaction of the above-mentioned glycosyl nitrates with cesium diphenyl phosphate leads to thermodynamically

  β-糖基二苄基磷酸酯的过乙酸盐在二苄基磷酸铯与衍生自 1-吡喃岩藻糖、d-吡喃半乳糖和 2-叠氮基-2-脱氧-d-吡喃半乳糖或三-O的过乙酰-α-糖基硝酸盐反应中有效形成-乙酰-α-1-吡喃岩藻糖基溴。相反，上述糖基硝酸盐与二苯基磷酸铯的反应通过相应β-端基异构体的中间体形成导致热力学上更稳定的α-糖基二苯基磷酸酯。