3-O-acetyl-1,2,3,5,6-pentadeoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-β-D-erythro-hexofuranuronosulfonic acid triethylammonium salt | 140175-62-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3-O-acetyl-1,2,3,5,6-pentadeoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-β-D-erythro-hexofuranuronosulfonic acid triethylammonium salt
• 英文别名: 2-[(2R,3S,5R)-3-acetyloxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]ethanesulfonic acid;N,N-diethylethanamine
• CAS: 140175-62-8
• 化学式: C₆H₁₅N*C₁₃H₁₈N₂O₈S
• 分子量: 463.552
• InChiKey: CRDGSVPMBMWTQX-QJQMQQLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.69
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  148.0
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  1-(2-deoxy-3-O-mesyl-5-O-tosyl-β-D-threo-pentofuranosyl)thymine 在 4-二甲氨基吡啶 、 ammonium hydroxide 、 乙炔锂乙二胺配合物 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 74.0h， 生成 3-O-acetyl-1,2,3,5,6-pentadeoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-β-D-erythro-hexofuranuronosulfonic acid triethylammonium salt
  参考文献：
  名称：

  Nucleoside sultones: synthons for the preparation of novel nucleotide analogs. 1. Synthesis and ring-opening reactions

  摘要：

  Treatment of either the 5'-O-tosyl or the 5'-O-mesyl derivative of 3'-O-mesylthymidine with lithium acetylide-ethylenediamine complex in DMSO affords the intramolecular 6,3-ester of 1,2,5,6-tetradeoxy-l-(3,4-dihydro-5-methyl-2, 4-dioxo-1(2H)-pyrimidinyl)-beta-D-erythro-hexofuranuronosulfonic acid (2). Similarly, the 5'-O-tosyl or 5'-O-mesyl derivative of 1-(2-deoxy-3-O-mesyl-beta-D-threo-pentofuranosyl)thymine affords the intramolecular 6,3-ester of 1,2,5,6-tetradeoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-beta-D-threo-hexofuranurononsulfonic acid (5). Sultone 5 reacts with a variety of nucleophiles to afford good yields of the corresponding 3'-substituted sulfonate salts (6, 7, 9, and 10) and, in some cases, the unsaturated nucleoside 8. Sultone 2 was generally much less susceptible to ring opening by nucleophiles. However, in the presence of base, nucleophilic substitution with azide ion did proceed via the intermediate anhydronucleoside, 11, to afford 6. Reaction of 2 with EtOH-NaOH afforded a 1:1 mixture of the epimeric 3'-hydroxy compounds 9 and 12. The above sulfonate salts represent interesting new isosteres of nucleoside 5'-O-phosphates.

  DOI：

  10.1021/jo00036a014