Diphenyl-acetic acid (2R,3S,5R)-2-diphenylacetoxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester | 444810-99-5

• 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: Diphenyl-acetic acid (2R,3S,5R)-2-diphenylacetoxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
• 英文别名: [(2R,3S,5R)-3-(2,2-diphenylacetyl)oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl 2,2-diphenylacetate
• CAS: 444810-99-5
• 化学式: C₃₈H₃₄N₂O₇
• 分子量: 630.697
• InChiKey: CHHUBNZMEDAVGH-DCMFLLSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  47
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Diphenyl-acetic acid (2R,3S,5R)-2-diphenylacetoxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 在 三氟甲磺酸三甲基硅酯 、 水 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 41.0h， 生成 [(2R,3S,5S)-3-(2,2-diphenylacetyl)oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl 2,2-diphenylacetate
  参考文献：
  名称：

  A convenient method for the conversion of β-thymidine to α-thymidine based on TMSOTf-mediated C1′-epimerization

  摘要：

  A practically useful method for the synthesis of alpha-thymidine from beta-thymidine was developed by trimethylsilyl triflate-mediated C1'-epimerization. When 5'-O-diphenylacetyl-3'-O-toluoylthmidine was trimethylsilylated and successively treated with TMSOTf in acetonitrile, the resulting a-thymidine derivative was crystallized and isolated without silica-gel column chromatography. Deprotection gave unprotected alpha-thymidine in an overall yield of 50% from beta-thymidine. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(02)00411-2
• 作为产物：
  描述：

  [(2R,3S,5S)-3-(2,2-diphenylacetyl)oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl 2,2-diphenylacetate 以 乙腈 为溶剂， 反应 20.0h， 生成 Diphenyl-acetic acid (2R,3S,5R)-2-diphenylacetoxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  A convenient method for the conversion of β-thymidine to α-thymidine based on TMSOTf-mediated C1′-epimerization

  摘要：

  A practically useful method for the synthesis of alpha-thymidine from beta-thymidine was developed by trimethylsilyl triflate-mediated C1'-epimerization. When 5'-O-diphenylacetyl-3'-O-toluoylthmidine was trimethylsilylated and successively treated with TMSOTf in acetonitrile, the resulting a-thymidine derivative was crystallized and isolated without silica-gel column chromatography. Deprotection gave unprotected alpha-thymidine in an overall yield of 50% from beta-thymidine. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(02)00411-2

文献信息

• A convenient method for the conversion of β-thymidine to α-thymidine based on TMSOTf-mediated C1′-epimerization
  作者：Yuichi Sato、Gohsuke Tateno、Kohji Seio、Mitsuo Sekine

  DOI：10.1016/s0040-4039(02)00411-2

  日期：2002.4

  A practically useful method for the synthesis of alpha-thymidine from beta-thymidine was developed by trimethylsilyl triflate-mediated C1'-epimerization. When 5'-O-diphenylacetyl-3'-O-toluoylthmidine was trimethylsilylated and successively treated with TMSOTf in acetonitrile, the resulting a-thymidine derivative was crystallized and isolated without silica-gel column chromatography. Deprotection gave unprotected alpha-thymidine in an overall yield of 50% from beta-thymidine. (C) 2002 Published by Elsevier Science Ltd.