methyl (3aS,4R,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate | 145372-65-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (3aS,4R,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate
• CAS: 145372-65-2
• 化学式: C₁₄H₂₂O₇
• 分子量: 302.324
• InChiKey: ULKMOMURHJZLPA-SAVGLBRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (3aS,4R,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate 在 溶剂黄146 、 过碘酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.17h， 生成 methyl (3aS,4R,6S,6aR)-6-formyl-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate
  参考文献：
  名称：

  Tetrahydrofuran amino acids—versatile building blocks for unnatural biopolymers: lack of secondary structure in oligomeric carbopeptoids derived from a D-galacto-5-(aminomethyl) tetrahydrofuran-2-carboxylic acid

  摘要：

  本文介绍了从七碳内酯中高效合成 D-半乳糖构型四氢呋喃氨基酸作为单体以生成序列确定的结构生物聚合物模拟物的方法。对这种单体的同源异构体衍生物特性的研究表明，它们并不具有明确的二级结构。此外，还介绍了异源同分异构体衍生物的意外形成及其溶液结构研究。

  DOI：

  10.1039/b002995p
• 作为产物：
  描述：

  2,3:5,6-二-O-异亚丙基-D-甘露糖酸-1,4-内酯 在 三乙基硅烷 、 三氟甲磺酸三甲基硅酯 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 methyl (3aS,4R,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate
  参考文献：
  名称：

  Furan-based synthesis of C-glycosyl carboxylates

  摘要：

  The installation of the 2-furyl ring at the anomeric carbon of 2,3,4,6-tetra-O-benzyl-D-glucopyranose and 2,3.5,6-di-O-isopropylidene-D-mannofuranose is carried out either by addition of 2-lithiofuran to the corresponding lactones either by direct C-glycosidation of the O-acetyl derivatives with furan; the resultant 2-furyl C-glycosides are converted to carboxylic acids by the oxidative cleavage of the furan nucleous.

  DOI：

  10.1016/s0040-4039(00)79320-8

文献信息

• The ring contraction of δ-lactones with leaving group α-substituents: a strategy for the synthesis of 2,5-disubstituted highly functionalised homochiral tetrahydrofurans
  作者：Sik-Man S. Choi、Paul M. Myerscough、Antony J. Fairbanks、Ben M. Skead、Claire J. F. Bichard、Simon J. Mantell、Jong Chan Son、George W. J. Fleet、John Saunders、David Brown

  DOI：10.1039/c39920001605

  日期：——

  Treatment of derivatives of δ-lactones having a leaving group at C-2 with methanol in the presence of base gives methyl tetrahydrofuran-α-carboxylates in good to excellent yield with a high degree of stereocontrol of the carbon substituents at C-2 and C-5.

  在碱存在下，用甲醇处理C-2位带有保护基的γ-内酯衍生物，可以得到甲基四氢呋喃-γ-羧酸酯，收率良好到极佳，且C-2和C-5位碳取代基具有高度的立体选择性。
• Tetrahydrofuran α-Azido Esters: Precursors of Anomeric α-Amino Acid Monomers via Radical Bromination
  作者：Martin D. Smith、Danile D. Long、Angeles Martín、Neil Campbell、Yves Blériot、George W. J. Fleet

  DOI：10.1055/s-1999-2766

  日期：1999.7
• Furan-based synthesis of C-glycosyl carboxylates
  作者：Alessandro Dondoni、Alberto Marra、Marie-Christine Scherrmann

  DOI：10.1016/s0040-4039(00)79320-8

  日期：1993.11

  The installation of the 2-furyl ring at the anomeric carbon of 2,3,4,6-tetra-O-benzyl-D-glucopyranose and 2,3.5,6-di-O-isopropylidene-D-mannofuranose is carried out either by addition of 2-lithiofuran to the corresponding lactones either by direct C-glycosidation of the O-acetyl derivatives with furan; the resultant 2-furyl C-glycosides are converted to carboxylic acids by the oxidative cleavage of the furan nucleous.
• Tetrahydrofuran amino acids—versatile building blocks for unnatural biopolymers: lack of secondary structure in oligomeric carbopeptoids derived from a D-galacto-5-(aminomethyl) tetrahydrofuran-2-carboxylic acid
  作者：Dominic E. A. Brittain、Mark P. Watterson、Timothy D. W. Claridge、Martin D. Smith、George W. J. Fleet

  DOI：10.1039/b002995p

  日期：——

  The efficient synthesis of a D-galacto-configured tetrahydrofuran amino acid from a seven-carbon lactone as a monomer for the generation of sequence-defined structured biopolymer mimics is described. Investigations into the characteristics of homooligomeric derivatives of this monomer indicate that they do not adopt well defined secondary structures. The unanticipated formation of a heterooligomeric derivative and investigations into its solution structure are also described.

  本文介绍了从七碳内酯中高效合成 D-半乳糖构型四氢呋喃氨基酸作为单体以生成序列确定的结构生物聚合物模拟物的方法。对这种单体的同源异构体衍生物特性的研究表明，它们并不具有明确的二级结构。此外，还介绍了异源同分异构体衍生物的意外形成及其溶液结构研究。