(1R,3R,4S,5S,7R)-4-[tert-butyl(dimethyl)silyl]oxy-1-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(2,4-dioxopyrimidin-1-yl)-2-oxa-9-thia-6-azaspiro[4.4]nonane-7-carboxylic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3R,4S,5S,7R)-4-[tert-butyl(dimethyl)silyl]oxy-1-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(2,4-dioxopyrimidin-1-yl)-2-oxa-9-thia-6-azaspiro[4.4]nonane-7-carboxylic acid
• 英文别名: (3R,5S,6R,8R,9S)-9-[tert-butyl(dimethyl)silyl]oxy-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-8-(2,4-dioxopyrimidin-1-yl)-7-oxa-1-thia-4-azaspiro[4.4]nonane-3-carboxylic acid
• 化学式: C₂₄H₄₃N₃O₇SSi₂
• 分子量: 573.858
• InChiKey: CDXKSZCXORNWQP-OZZOQKJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  152
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (1R,3R,4S,5S,7R)-4-[tert-butyl(dimethyl)silyl]oxy-1-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(2,4-dioxopyrimidin-1-yl)-2-oxa-9-thia-6-azaspiro[4.4]nonane-7-carboxylic acid 在 N-羟基丁二酰亚胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以96%的产率得到(3R,5S,6R,8R,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-8-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-7-oxa-1-thia-4-aza-spiro[4.4]nonane-3-carboxylic acid amide
  参考文献：
  名称：

  Novel Spironucleosides: 1″,3″-Thiazolidine-2″-Spiro-3′-3′-Deoxyuridine Derivatives

  摘要：

  Reaction of 2',5'-di-O-TBDMS-3'-ketouridine 1 with L-cysteine yielded in good yield a resolvable mixture of the two expected epimeric spironucleosides 2 and 3. Amidification of their carboxylic group took place readily and the ribo carboxamide 4 was oxidized to the corresponding sulfoxide 6. Despite their similarity to TSAO derivatives these compounds did not exhibit usable anti-HIV activity.

  DOI：

  10.1080/07328319808004224
• 作为产物：
  描述：

  L-半胱氨酸 、 2',5'-bis-O-tert-butyldimethylsilyl-3'-ketouridine 在 叔丁基二甲基氯硅烷 作用下， 生成 (1R,3R,4S,5S,7R)-4-[tert-butyl(dimethyl)silyl]oxy-1-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(2,4-dioxopyrimidin-1-yl)-2-oxa-9-thia-6-azaspiro[4.4]nonane-7-carboxylic acid 、 (3R,5R,6R,8R,9S)-9-[tert-butyl(dimethyl)silyl]oxy-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-8-(2,4-dioxopyrimidin-1-yl)-7-oxa-1-thia-4-azaspiro[4.4]nonane-3-carboxylic acid
  参考文献：
  名称：

  Novel Spironucleosides: 1″,3″-Thiazolidine-2″-Spiro-3′-3′-Deoxyuridine Derivatives

  摘要：

  Reaction of 2',5'-di-O-TBDMS-3'-ketouridine 1 with L-cysteine yielded in good yield a resolvable mixture of the two expected epimeric spironucleosides 2 and 3. Amidification of their carboxylic group took place readily and the ribo carboxamide 4 was oxidized to the corresponding sulfoxide 6. Despite their similarity to TSAO derivatives these compounds did not exhibit usable anti-HIV activity.

  DOI：

  10.1080/07328319808004224

文献信息

• Novel Spironucleosides: 1″,3″-Thiazolidine-2″-Spiro-3′-3′-Deoxyuridine Derivatives
  作者：Jean M. J. Tronchet、Imre Kovács、Françoise Barbalat-Rey、Margarita VegaHolm

  DOI：10.1080/07328319808004224

  日期：1998.6

  Reaction of 2',5'-di-O-TBDMS-3'-ketouridine 1 with L-cysteine yielded in good yield a resolvable mixture of the two expected epimeric spironucleosides 2 and 3. Amidification of their carboxylic group took place readily and the ribo carboxamide 4 was oxidized to the corresponding sulfoxide 6. Despite their similarity to TSAO derivatives these compounds did not exhibit usable anti-HIV activity.