3S,5S-5-(t-butyldiphenylsiloxymethyl)-3-methyl-4,5-dihydro-2(3H)-furanone | 147200-09-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3S,5S-5-(t-butyldiphenylsiloxymethyl)-3-methyl-4,5-dihydro-2(3H)-furanone
• 英文别名: 5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-C-methyl-D-erythro-pentonic-γ-lactone；(3S,5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-3-methyldihydrofuran-2(3H)-one；(3S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-methyloxolan-2-one
• CAS: 147200-09-7
• 化学式: C₂₂H₂₈O₃Si
• 分子量: 368.548
• InChiKey: XBHGPYCZPIKCFG-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3S,5S-5-(t-butyldiphenylsiloxymethyl)-3-methyl-4,5-dihydro-2(3H)-furanone 在 吡啶 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 7.33h， 生成 9-(2,3-dideoxy-2-C-methyl-β-D-erythro-pentofuranosyl)adenine
  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
• 作为产物：
  描述：

  5-(羟基甲基)二氢-2(3H)-呋喃酮 在 palladium on activated charcoal 吡啶 、 水 、 氢气 、 双氧水 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， -78.0~25.0 ℃ 、1000.0 kPa 条件下， 反应 9.25h， 生成 3S,5S-5-(t-butyldiphenylsiloxymethyl)-3-methyl-4,5-dihydro-2(3H)-furanone
  参考文献：
  名称：

  Enantiopure DAVA-derivatives-part III. Synthesis of all 4 stereoisomers of 2-methyl-4-hydroxy-5-aminopentanoic acid (2-Me-4-OH-DAVA).

  摘要：

  A stereoselective synthesis of the 4 stereoisomers of 2-methyl-4-hydroxy-5-amino-pentanoic acid namely 2R,4S-9a, 2S,4S-9b, ent-9a and ent-9b is presented, starting from the known lactones S-1 and R-l, which are readily available from L- and D-glutamic acid. Only ent-9b shows affinity for GABA(B)-receptor sites.

  DOI：

  10.1016/s0957-4166(00)86022-x

文献信息

• Novel Bicyclic Pyridinones
  申请人：Pfizer Inc.

  公开号：US20140088111A1

  公开（公告）日：2014-03-27

  Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula I as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

  所述化合物及其药用可接受盐已被披露，其中所述化合物具有规范中定义的Formula I结构。相应的药用组合物、治疗方法、合成方法和中间体也已被披露。
• Design, synthesis, and cytotoxicity of stabilized mycolactone analogs
  作者：Vaddela Sudheer Babu、Ya Zhou、Yoshito Kishi

  DOI：10.1016/j.bmcl.2017.01.036

  日期：2017.3

  On exposure to visible light, mycolactone A/B, the causative toxin of Buruli ulcer, rearranges to a mixture of four photo-mycolactones apparently via a rare photochemically-induced [4πs + 2πa] cycloaddition. In order to prevent the rearrangement, two C6′-C7′ dihydromycolactone analogs 6′α-15 and 6′β-15 were designed and synthesized. 6′α-15 and 6′β-15 were shown to be stable under not only photochemical

  上经由罕见光化学诱导的[明显暴露于可见光，细菌内酯A / B，布鲁里溃疡的致病毒素，重排的四个光电-mycolactones混合物4个π小号 +  2 π一个]环加成。为了防止重排，设计并合成了两个C6'-C7'二氢霉菌内酯类似物6'α- 15和6'β- 15。6′α- 15和6′β- 15不仅在光化学条件下，而且在酸性和碱性条件下均显示稳定。测试了针对任意选择的四种细胞系（人Hek-293，人肺癌A-549，人黑素瘤LOX-IMVI和小鼠L-929）的细胞毒性，从而揭示：（1）两种类似物均保持有效的细胞毒性；（2）6'β- 15对人类细胞系的效力显着高于6'α- 15；（3）与亲本支链内酯A / B相比，6'β- 15对人Hek-293表现出相同的效力，而对人肺癌A-549和人黑素瘤LOX-IMVI的效力明显较低。
• Lactols in stereoselection 3
  作者：Katsuhiko Tomooka、Tatsuyuki Okinaga、Keisuke Suzuki、Gen-ichi Tsuchihashi

  DOI：10.1016/s0040-4039(00)99520-0

  日期：1989.1

  addition of MeTi(O-iPr)3 to α-chiral lactols proceeds in highly diastereoselective manner. The sense of the diastereofacial selection is anti-Cram-type, which provides a new and useful method for 1,2-asymmetric induction.

  MeTi（O-iPr）3的亲核加成反应以高度非对映选择性的方式进行。非对面选择的意义是反克拉姆式的，这为1，2-不对称诱导提供了一种新的有用的方法。
• [EN] 2',3'-DIDEOXY-2'-α-FLUORO-2'-&bgr;-C-METHYLNUCLEOSIDES AND PRODRUGS THEREOF<br/>[FR] 2',3'-DIDÉSOXY-2'-A-FLUORO-2'-SS-C-MÉTHYLNUCLÉOSIDES ET LEURS PROMÉDICAMENTS
  申请人：NANJING MOLECULAR RES INC

  公开号：WO2013013009A3

  公开（公告）日：2014-05-08
• 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.