(S)-methyl 2-((S)-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)(hydroxy)methyl)-2-methylpent-4-enoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (S)-methyl 2-((S)-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)(hydroxy)methyl)-2-methylpent-4-enoate
• 英文别名: methyl (2S)-2-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-hydroxymethyl]-2-methylpent-4-enoate
• 化学式: C₁₃H₂₂O₅
• 分子量: 258.315
• InChiKey: BLGABFRTODOFDR-BREBYQMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-((S)-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)(hydroxy)methyl)-2-methylpent-4-enoate 在 吡啶 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 高碘酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 5.25h， 生成 (R)-2-((S)-1-((2-methoxyethoxy)methoxy)-2-oxoethyl)-2-methylpent-4-en-1-yl benzoate
  参考文献：
  名称：

  Dual-Face Nucleoside Scaffold Featuring a Stereogenic All-Carbon Quaternary Center. Intramolecular Silicon Tethered Group-Transfer Reaction

  摘要：

  The design of a novel nucleoside scaffold that exhibits an all-carbon quaternary center is reported. This allows for both alpha- and beta-anomers of a given 2'-deoxy-2',2'-difluoro nucleoside analog (NA) to have potential biological activity. Using an intramolecular atom-transfer reaction, an all-carbon quaternary center was obtained without the use of heavy metals and/or harsh conditions. The chemistry developed is efficient, easily scalable and leads to novel libraries of molecules.

  DOI：

  10.1021/ol502777r
• 作为产物：
  描述：

  methyl (3R)-2-bromo-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-[dimethyl(prop-2-enyl)silyl]oxy-2-methylpropanoate 在 三乙基硼 、 C.I.酸性橙108 、 triethylamine tris(hydrogen fluoride) 作用下， 以 甲苯 为溶剂， 反应 4.5h， 以85%的产率得到(S)-methyl 2-((S)-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)(hydroxy)methyl)-2-methylpent-4-enoate
  参考文献：
  名称：

  Dual-Face Nucleoside Scaffold Featuring a Stereogenic All-Carbon Quaternary Center. Intramolecular Silicon Tethered Group-Transfer Reaction

  摘要：

  The design of a novel nucleoside scaffold that exhibits an all-carbon quaternary center is reported. This allows for both alpha- and beta-anomers of a given 2'-deoxy-2',2'-difluoro nucleoside analog (NA) to have potential biological activity. Using an intramolecular atom-transfer reaction, an all-carbon quaternary center was obtained without the use of heavy metals and/or harsh conditions. The chemistry developed is efficient, easily scalable and leads to novel libraries of molecules.

  DOI：

  10.1021/ol502777r

文献信息

• NUCLEOSIDE ANALOGUES AND METHODS OF USE THEREOF
  申请人：LCB PHARMA INC.

  公开号：US20190322693A1

  公开（公告）日：2019-10-24

  Nucleoside analogues that can be used as anticancer or antiviral agents are presented. These compounds are nucleoside and/or nucleotide prodrugs. In particular, the subject matter relates to nucleoside analogues comprising a tetrahydrofuranyl, or tetrahydrothienyl moiety which: have a quaternary stereogenic all-carbon center at the 3′ position and bear a phosphoryl group at either one of, or both of positions C5′ and/or C3′; have a quaternary stereogenic all-carbon center at one of the 3′ position, 2′ position, or no quaternary stereogenic center at all, and bear a β-blocked lipoate derivative attached through an amide bond to the primary amine of the nucleobase; or have a quaternary stereogenic all-carbon center at the 2′ position and bear a phosphorylated prodrug at the C5′-position and a β-blocked lipoate derivative attached through an amide bond to the primary amine of the nucleobase.
• Dual-Face Nucleoside Scaffold Featuring a Stereogenic All-Carbon Quaternary Center. Intramolecular Silicon Tethered Group-Transfer Reaction
  作者：Guillaume Tambutet、Fabiola Becerril-Jiménez、Starr Dostie、Ryan Simard、Michel Prévost、Philippe Mochirian、Yvan Guindon

  DOI：10.1021/ol502777r

  日期：2014.11.7

  The design of a novel nucleoside scaffold that exhibits an all-carbon quaternary center is reported. This allows for both alpha- and beta-anomers of a given 2'-deoxy-2',2'-difluoro nucleoside analog (NA) to have potential biological activity. Using an intramolecular atom-transfer reaction, an all-carbon quaternary center was obtained without the use of heavy metals and/or harsh conditions. The chemistry developed is efficient, easily scalable and leads to novel libraries of molecules.