2,2-dimethylpropionic acid 2,3-dihydrofuran-2-ylmethyl ester | 144867-90-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 2,2-dimethylpropionic acid 2,3-dihydrofuran-2-ylmethyl ester
• 英文别名: 1,4-anhydro-2,3-dideoxy-D-pent-1-enitol 5-trimethylacetate；2-pivaloyloxymethyl-2,3-dihydrofuran；[(2S)-2,3-dihydrofuran-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 144867-90-3
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: NPWJOWATAWELMH-QMMMGPOBSA-N

物化性质

• 沸点：
  236.1±19.0 °C(Predicted)
• 密度：
  1.022±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  2,2-dimethylpropionic acid 2,3-dihydrofuran-2-ylmethyl ester 在 palladium on activated charcoal N-碘代丁二酰亚胺 、 氢气 、 sodium methylate 、 四氯化锡 作用下， 以 甲醇 、 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 9.0h， 生成 2',3'-双脱氧腺苷
  参考文献：
  名称：

  通过呋喃类糖基中间体轻松，高度立体选择性地合成2'，3'-二脱氧-和2'，3'-二氢化-2'，3t'-二脱氧核苷

  摘要：

  对呋喃糖基糖醛10的区域特异性和高度立体选择性的亲电加成反应已被用作合成ddA和d4T抗病毒核苷的关键步骤。

  DOI：

  10.1016/0040-4039(92)89018-8
• 作为产物：
  描述：

  (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 在 吡啶 、 氯化亚砜 、 potassium tert-butylate 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 2,2-dimethylpropionic acid 2,3-dihydrofuran-2-ylmethyl ester
  参考文献：
  名称：

  通过呋喃类糖基中间体轻松，高度立体选择性地合成2'，3'-二脱氧-和2'，3'-二氢化-2'，3t'-二脱氧核苷

  摘要：

  对呋喃糖基糖醛10的区域特异性和高度立体选择性的亲电加成反应已被用作合成ddA和d4T抗病毒核苷的关键步骤。

  DOI：

  10.1016/0040-4039(92)89018-8

文献信息

• Asymmetric Synthesis of Nucleosides via Molybdenum-Catalyzed Alkynol Cycloisomerization Coupled with Stereoselective Glycosylations of Deoxyfuranose Glycals and 3-Amidofuranose Glycals
  作者：Frank E. McDonald、Mark M. Gleason

  DOI：10.1021/ja960581l

  日期：1996.1.1

  effects of 3-amido-2,3-dideoxyfuranose glycals were exploited in a novel and highly stereoselective synthesis strategy for a variety of biologically active 3‘-amino-2‘,3‘-dideoxy- and 3‘-amino-3‘-deoxy-β-nucleosides, including puromycin aminonucleoside. In addition, the mechanism of the molybdenum-catalyzed alkynol cycloisomerization reaction has been studied. Evidence is p...

  脱氧呋喃糖糖可以通过五羰基钼催化的炔醇环异构化有效制备，炔醇很容易通过短合成序列制备成手性非外消旋形式，其特征是市售烯丙醇的不对称环氧化。环异构化反应被证明与酯和酰胺官能团相容。2,3-二脱氧呋喃糖苷被立体选择性地转化为抗艾滋病 β-核苷司他夫定 (2',3'-didehydro-2',3'-dideoxythymidine, d4T) 和抗病毒药物 3'-脱氧-β-核苷虫草素. 3-amido-2,3-dideoxyfuranose 聚糖的异嵌合和氢键导向作用被用于各种具有生物活性的 3'-amino-2',3'-dideoxy-和3'-氨基-3'-脱氧-β-核苷，包括嘌呤霉素氨基核苷。此外，还研究了钼催化炔醇环异构化反应的机理。证据是...
• Processes for preparation of nucleoside derivatives
  申请人：Bristol-Myers Squibb Company

  公开号：EP0501511A2

  公开（公告）日：1992-09-02

  Improved processes for production of useful nucleoside derivatives of formula (VI) wherein B1 is a pyrimidinyl group of Formula XXI or a purinyl group of Formula XXII, in which V is amino or hydroxy, R2 is hydrogen or methyl, and R3 is hydrogen or amino;

  改进了生产公式（VI）中有用的核苷衍生物的过程，其中B1是公式XXI的嘧啶基团或公式XXII的嘌呤基团，其中V是氨基或羟基，R2是氢或甲基，R3是氢或氨基。
• McDonald, Frank E.; Gleason, Mark M., Angewandte Chemie, 1995, vol. 107, # 3, p. 356 - 358
  作者：McDonald, Frank E.、Gleason, Mark M.

  DOI：——

  日期：——
• Furanoid Glycal as a Starting Material for Nucleoside Derivatives
  作者：Hiroshi Kawakami、Takashi Ebata、Koshi Koseki、Koji Okano、Katsuya Matsumoto、Hajime Matsushita

  DOI：10.3987/com-93-6503

  日期：——

  Furanoid glycal was utilized as a starting material for the nucleoside derivatives with the aid of benzenesulfenyl chloride. Condensation reaction with silylated nucleic bases was high in the presence of SnCl4. Electrophilic addition of benzenesulfenyl chloride to the glycal with substituent also proceeded in high stereoselectivity. Phenylthio-substituted nucleoside was used to convert 2',3'-dideoxynucleoside and 2',3'-didehydro-2',3'-dideoxynucleoside.
• A Rh(I)-Catalyzed Cycloisomerization of Homo- and Bis-homopropargylic Alcohols
  作者：Barry M. Trost、Young Ho Rhee

  DOI：10.1021/ja0344258

  日期：2003.6.1

  The ability to form rhodium-vinylidene complexes in situ from terminal alkynes has led to the development of a catalytic process, the cycloisomerization of homopropargylic and bis-homopropargylic alcohols to dihydrofurans and dihydropyrans. Among the transition metals that perform similar reactions, rhodium catalysts demonstrate the best chemoselectivity and turnover numbers to date. Both secondary and tertiary alcohols participate equally well. The presence of proparylic oxygen and nitrogen functionality, which potentially can be induced to ionize via formation of allenylidene metal complexes, is compatible with this catalyst. The formation of a 5-amino-dihydropyran which is not compatible with some of the previous catalysts proceeds in good yield with the rhodium catalysts. A substrate bearing a benzylic hydroxyl group adjacent to an electron-rich aromatic ring also participates without complications of ionization. The method provides access to useful aminosugars. A mechanism to account for the different selectivity of this catalyst as compared to others is proposed.