5'-O-mesyl-2,3'-anhydro-thymidine | 15981-86-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5'-O-mesyl-2,3'-anhydro-thymidine
• 英文别名: [(1R,9S,10R)-4-methyl-5-oxo-8,11-dioxa-2,6-diazatricyclo[7.2.1.02,7]dodeca-3,6-dien-10-yl]methyl methanesulfonate
• CAS: 15981-86-9
• 化学式: C₁₁H₁₄N₂O₆S
• 分子量: 302.308
• InChiKey: JLNYOOGYXGODSD-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3',5'-二-O-甲磺酰基胸苷 在 乙炔锂乙二胺配合物 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 以35%的产率得到1,2,5,6-tetradeoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-β-D-erythro-hexofuranurono-6,3-sultone
  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

文献信息

• Nucleoside sultones: synthons for the preparation of novel nucleotide analogs. 1. Synthesis and ring-opening reactions
  作者：Peter A. Crooks、Robert C. Reynolds、Joseph A. Maddry、Anita Rathore、M. Shamim Akhtar、John A. Montgomery、John A. Secrist

  DOI：10.1021/jo00036a014

  日期：1992.5

  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.