5-O-benzyl-2,3-dideoxy-2-C-methyl-D-threo-pentonic-γ-lactone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-O-benzyl-2,3-dideoxy-2-C-methyl-D-threo-pentonic-γ-lactone
• 英文别名: (3R,5S)-3-methyl-5-(phenylmethoxymethyl)oxolan-2-one
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: GBGPWVYIQOHUSE-PWSUYJOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-(羟基甲基)二氢-2(3H)-呋喃酮 在 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 5-O-benzyl-2,3-dideoxy-2-C-methyl-D-threo-pentonic-γ-lactone
  参考文献：
  名称：

  Synthesis of 2′-C-α-Methyl-2′,3′-dideoxynucleosides

  摘要：

  A general method for the synthesis of 2'-C-alpha-methyl-2',3'-dideoxynucleosides is presented. Stereofacial selectivity of the 2-C-methylation reaction of gamma-lactone has been investigated, in which the presence of a bulky group at the 5-hydroxymethyl produced the alpha-isomer as a major product. During glycosylation, the alpha-methyl group directed the formation of nucleosides in favor of the beta-isomer. This methodology is applied to the synthesis of some new pyrimidine and purine nucleosides.

  DOI：

  10.1080/07328319608002379

文献信息

• Stereoselective kinetic protonation of chiral γ-lactone enolates
  作者：Seiichi Takano、Junko Kudo、Michiyasu Takahashi、Kunio Ogasawara

  DOI：10.1016/s0040-4039(00)84541-4

  日期：——

  When lithium enolates generated from five chiral α, γ-disubstituted γ-lactones are treated with proton sources, formation of the α, γ-syn epimers always predominates over the a,y-anti epimers in ratios of 10.2–2.9:1. Higher syn/anti ratios are obtained via silyl enolates in some cases. Chirality discrimination by chiral proton source is also observed in particular cases.

  当用质子源处理由五个手性α，γ-二取代的γ-内酯生成的烯醇锂时，α，γ-syn差向异构体的形成总是比a，y-反差向异构体占10.2-2.9：1。在某些情况下，通过甲硅烷基烯醇化物可获得更高的顺/反比。在特定情况下，还观察到通过手性质子源进行手性区分。
• PROCESSES AND INTERMEDIATES FOR THE PREPARATION OF 1'-CYANO-CARBANUCLEOSIDE ANALOGS
  申请人：Gilead Sciences, Inc.

  公开号：EP2480559B1

  公开（公告）日：2013-07-03
• Synthesis of 2′-C-α-Methyl-2′,3′-dideoxynucleosides
  作者：Indrajit Giri、Pascal J. Bolon、Chung K. Chu

  DOI：10.1080/07328319608002379

  日期：1996.1

  A general method for the synthesis of 2'-C-alpha-methyl-2',3'-dideoxynucleosides is presented. Stereofacial selectivity of the 2-C-methylation reaction of gamma-lactone has been investigated, in which the presence of a bulky group at the 5-hydroxymethyl produced the alpha-isomer as a major product. During glycosylation, the alpha-methyl group directed the formation of nucleosides in favor of the beta-isomer. This methodology is applied to the synthesis of some new pyrimidine and purine nucleosides.