(2S,3aR,8aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methyl-6-oxo-1,2,3a,8a-tetrahydro-6H-8-oxa-3,3b,7-triaza-cyclopenta[a]indene-3-carboxylic acid tert-butyl ester | 334024-77-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2S,3aR,8aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methyl-6-oxo-1,2,3a,8a-tetrahydro-6H-8-oxa-3,3b,7-triaza-cyclopenta[a]indene-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2R,4S,6S)-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-11-methyl-10-oxo-7-oxa-1,3,9-triazatricyclo[6.4.0.02,6]dodeca-8,11-diene-3-carboxylate
• CAS: 334024-77-0
• 化学式: C₃₁H₃₉N₃O₅Si
• 分子量: 561.753
• InChiKey: GQYLRANHMIPZMK-RIACCQAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  40.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  82.89
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2S,3aR,8aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methyl-6-oxo-1,2,3a,8a-tetrahydro-6H-8-oxa-3,3b,7-triaza-cyclopenta[a]indene-3-carboxylic acid tert-butyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以73%的产率得到(2R,3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective synthesis of azanucleosides aza-stavudine (aza-D4T), aza-2′,3′-didehydro-3′-deoxyuridine (aza-D4U), and its hydrogenated analogues from an endocyclic enecarbamate

  摘要：

  The stereoselective synthesis of the aza-analogues of nucleosides stavudine (D4T) and dideoxyuridine (DDU) were accomplished in a very concise manner (3-4 step sequences) with high overall yields from a five-membered endocyclic enecarbamate employing phenylselenenyl bromide as an effective promoter. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02343-1
• 作为产物：
  描述：

  5-甲基-1,3-二(三甲基硅烷基)-2,4(1H,3H)-嘧啶二酮 在 N-碘代丁二酰亚胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,3aR,8aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methyl-6-oxo-1,2,3a,8a-tetrahydro-6H-8-oxa-3,3b,7-triaza-cyclopenta[a]indene-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective synthesis of azanucleosides aza-stavudine (aza-D4T), aza-2′,3′-didehydro-3′-deoxyuridine (aza-D4U), and its hydrogenated analogues from an endocyclic enecarbamate

  摘要：

  The stereoselective synthesis of the aza-analogues of nucleosides stavudine (D4T) and dideoxyuridine (DDU) were accomplished in a very concise manner (3-4 step sequences) with high overall yields from a five-membered endocyclic enecarbamate employing phenylselenenyl bromide as an effective promoter. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02343-1