(3S,5S)-3-methyl-5-(phenylmethoxymethyl)oxolan-2-one | 107696-75-3

• 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: (3S,5S)-3-methyl-5-(phenylmethoxymethyl)oxolan-2-one
• CAS: 107696-75-3；107696-78-6；116060-82-3；116060-83-4；116696-29-8
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: GBGPWVYIQOHUSE-JQWIXIFHSA-N

物化性质

• 沸点：
  357.3±15.0 °C(predicted)
• 密度：
  1.096±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

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：

  (R)-苄氧甲基环氧乙烷 在 硫酸 、 (R)-苄氧甲基环氧乙烷 、 lithium chloride 、 lithium diisopropyl amide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 12.5h， 生成 (3S,5S)-3-methyl-5-(phenylmethoxymethyl)oxolan-2-one
  参考文献：
  名称：

  Practical Syntheses of Enantiomerically Enriched γ-Lactones and γ-Hydroxy Ketones by the Alkylation of Pseudoephedrine Amides with Epoxides and Their Derivatives

  摘要：

  Pseudoephedrine amide enolates are shown to undergo efficient alkylation reactions with epoxides as electrophiles. Reactions with monosubstituted epoxides are subject to stereochemical matching such that the pairing leading to the 1,3-syn diastereomer is a highly selective, synthetically useful process, while the pairing forming the 1,3-anti diastereomer is not. Reactions with the 1,1-disubstituted epoxide isobutylene oxide are also highly diastereoselective and synthetically useful, but ethylene oxide exhibits poor diastereoselectivity. As an alternative to the use of ethylene oxide, 2-(tert-butyldimethylsilyloxy)ethyl iodide is shown to undergo highly diastereoselective and efficient alkylation reactions with pseudoephedrine amide enolates. Interestingly, epoxides and alkyl halides are found to attack opposite pi-faces of pseudoephedrine amide enolates. The products of each of these alkylation reactions are transformed efficiently into gamma-lactones by acidic hydrolysis and into methyl ketones by the addition of methyllithium. The methodology described provides useful procedures for the synthesis of enantiomerically enriched gamma-lactones and gamma-hydroxy ketones.

  DOI：

  10.1021/jo952032o

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。
• [EN] IMIDAZOTRIAZINE DERIVATIVES AS CD73 INHIBITORS<br/>[FR] DÉRIVÉS D'IMIDAZOTRIAZINE EN TANT QU'INHIBITEURS DE CD73
  申请人：BIOARDIS LLC

  公开号：WO2020210970A1

  公开（公告）日：2020-10-22

  The present disclosure relates generally to imidazotriazine derivatives that are inhibitors of CD73 and are useful in treating CD73-associated diseases or conditions. Compositions containing the compounds of the present disclosure are also provided.

  本公开涉及一般为CD73抑制剂的咪唑三嗪衍生物，可用于治疗CD73相关的疾病或病情。本公开还提供了含有本公开化合物的组合物。
• 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.
• Practical Syntheses of Enantiomerically Enriched γ-Lactones and γ-Hydroxy Ketones by the Alkylation of Pseudoephedrine Amides with Epoxides and Their Derivatives
  作者：Andrew G. Myers、Lydia McKinstry

  DOI：10.1021/jo952032o

  日期：1996.1.1

  Pseudoephedrine amide enolates are shown to undergo efficient alkylation reactions with epoxides as electrophiles. Reactions with monosubstituted epoxides are subject to stereochemical matching such that the pairing leading to the 1,3-syn diastereomer is a highly selective, synthetically useful process, while the pairing forming the 1,3-anti diastereomer is not. Reactions with the 1,1-disubstituted epoxide isobutylene oxide are also highly diastereoselective and synthetically useful, but ethylene oxide exhibits poor diastereoselectivity. As an alternative to the use of ethylene oxide, 2-(tert-butyldimethylsilyloxy)ethyl iodide is shown to undergo highly diastereoselective and efficient alkylation reactions with pseudoephedrine amide enolates. Interestingly, epoxides and alkyl halides are found to attack opposite pi-faces of pseudoephedrine amide enolates. The products of each of these alkylation reactions are transformed efficiently into gamma-lactones by acidic hydrolysis and into methyl ketones by the addition of methyllithium. The methodology described provides useful procedures for the synthesis of enantiomerically enriched gamma-lactones and gamma-hydroxy ketones.