甲基3-氨基-3-脱氧-1,2-O-异亚丙基-alpha-D-呋喃木酮糖酸酯 | 800379-24-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 甲基3-氨基-3-脱氧-1,2-O-异亚丙基-alpha-D-呋喃木酮糖酸酯
• 中文别名: (1E,2R,4E)-1,4-二(肟基)丁烷-2-醇
• 英文名称: methyl 3-amino-3-deoxy-1,2-O-(1-methylethylidne)-α-D-xylofuranoate
• 英文别名: methyl (3aR,5S,6R,6aR)-6-amino-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carboxylate
• CAS: 800379-24-2
• 化学式: C₉H₁₅NO₅
• 分子量: 217.222
• InChiKey: AFLKRDRKODOMQT-LZCNBPATSA-N

物化性质

• 沸点：
  275.1±40.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲基3-氨基-3-脱氧-1,2-O-异亚丙基-alpha-D-呋喃木酮糖酸酯 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 (3aR,5S,6R,6aR)-6-[((3aR,5S,6R,6aR)-6-Azido-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbonyl)-amino]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carboxylic acid
  参考文献：
  名称：

  Formation of a Stable 14-Helix in Short Oligomers of Furanoid cis-β-Sugar-Amino Acid

  摘要：

  Oligomers of a new class of sugar amino acids (SAA) using a xylofuranoic acid has been shown to generate a robust 14-helix. The design involved the use of xylofuranose with a cis arrangement between the amine and carboxyl groups to promote the adoption of a 14-helix instead of a mixed 12/10-helix observed in a sugar oligomer using a ribofuranoic acid and beta-Ala. The observation of a stable right-handed 14-helix in a cis-SAA is unprecedented.

  DOI：

  10.1021/ja0467667
• 作为产物：
  描述：

  3-azido-3-deoxy-1,2-O-isopropylidene-α-D-xylo-furanoic acid 在 palladium on activated charcoal 氢气 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 生成 甲基3-氨基-3-脱氧-1,2-O-异亚丙基-alpha-D-呋喃木酮糖酸酯
  参考文献：
  名称：

  Formation of a Stable 14-Helix in Short Oligomers of Furanoid cis-β-Sugar-Amino Acid

  摘要：

  Oligomers of a new class of sugar amino acids (SAA) using a xylofuranoic acid has been shown to generate a robust 14-helix. The design involved the use of xylofuranose with a cis arrangement between the amine and carboxyl groups to promote the adoption of a 14-helix instead of a mixed 12/10-helix observed in a sugar oligomer using a ribofuranoic acid and beta-Ala. The observation of a stable right-handed 14-helix in a cis-SAA is unprecedented.

  DOI：

  10.1021/ja0467667

文献信息

• Synthesis and Self-Assembly of Bolaamphiphiles Based on<i>β</i>-Amino Acids or an Alcohol
  作者：Prathama S. Mainkar、Chirumarry Sridhar、Ambadi Sudhakar、Srivari Chandrasekhar

  DOI：10.1002/hlca.201200060

  日期：2013.1

  The synthesis of bolaamphiphiles from unusual β‐amino acids or an alcohol and C12 or C20 spacers is described. Unusual β‐amino acids such as a sugar amino acid, an AZT‐derived amino acid, a norbornene amino acid, and an AZT‐derived amino alcohol were coupled with spacers under standard conditions to get the novel bolaamphiphiles 5–8 (Scheme 1), 12 and 13 (Scheme 2), and 17 and 20 (Scheme 3). Some of

  描述了由不常见的β-氨基酸或醇与C 12或C 20间隔基合成硼两亲分子的方法。不寻常的β-氨基酸，例如糖氨基酸，AZT衍生的氨基酸，氨基酸降冰片烯，和AZT衍生的氨基醇偶联在标准条件下垫片，以获得新颖bolaamphiphiles 5 - 8（方案1） ，12和13（方案2）以及17和20（方案3）。这些化合物中的一些，从MeOH / H 2沉淀时O，自组装成有组织的分子结构。
• Total Synthesis of Azumamide E and Sugar Amino Acid-Containing Analogue
  作者：Srivari Chandrasekhar、Chennamaneni Lohitha Rao、Mallikanti Seenaiah、Police Naresh、Bharatam Jagadeesh、Dharani Manjeera、Arpita Sarkar、Manika Pal Bhadra

  DOI：10.1021/jo8020264

  日期：2009.1.2

  An efficient and practical total synthesis of marine cyclic tetrapeptide, natural product azumamide E (1) is achieved via high-yielding reactions. The strategy also allowed us to synthesize the azumamide E-SAA (sugar amino acid) analogue (2), whose solution-phase NMR and biological activity studies were also carried out.

  通过高产率反应，可以有效，实用地合成海洋环四肽，天然产物氮酰胺E（1）。该策略还使我们能够合成the酰胺E-SAA（糖氨基酸）类似物（2），其溶液相NMR和生物活性研究也已进行。
• Backbone Regulation Mimicry by β-Peptidic Foldamers: Formation of a 10-Helix in a Mixed 6-Strand/14-Helix Conformational Pool
  作者：Bharatam Jagadeesh、Marelli Udaya Kiran、Ambadi Sudhakar、Srivari Chandrasekhar

  DOI：10.1002/chem.200902332

  日期：2009.11.23

  Hybrid β‐peptide foldamer: Detailed NMR spectroscopy studies have revealed the formation of a new class of 10‐helix in hybrid β‐peptidic assembly comprised of 6‐strand and 14‐helical nucleating motifs. These findings show a new means of accessing intermediate secondary structures and also mimic backbone regulations in biomolecules.

  杂合β肽折叠剂：详细的NMR光谱研究表明，杂合β肽装配中由6链和14螺旋成核基序组成的一类新的10螺旋形成了。这些发现显示出一种访问中间二级结构的新方法，并且还可以模拟生物分子中的骨架调节。
• Synthesis and Conformational Studies of a Hybrid Cyclic Peptide Based on<i>cis</i>-<i>β</i>-Furanoid Sugar Amino Acid (FSAA) and Ornithine
  作者：Srivari Chandrasekhar、Birudaraju Saritha、Police Naresh、Marelli Udayakiran、Chada Raji Reddy、Bharatam Jagadeesh

  DOI：10.1002/hlca.200890138

  日期：2008.7

  The conformational control of a 14-helix nucleating template, cis-β-furanoid sugar amino acid (FSAA), over a flexible δ-amino acid, ornithine is studied in a FSAA-ornithine cyclic tetrapeptide. Extensive NMR and MD studies reveal that the cyclic peptide adopts a three-dimentional bowl-shape cavity, which promotes six- and seven-membered intra- and inter-residue H-bonding, in polar and non-polar solvents

  一个的构象控制14螺旋成核模板，顺式- β -furanoid糖氨基酸（FSAA），在具有柔性的δ -氨基丁酸，鸟氨酸是在FSAA鸟氨酸环四肽的研究。广泛的NMR和MD研究表明，该环状肽采用三维碗形腔，可在极性和非极性溶剂中分别促进六元和七元残基内部和残基之间的氢键结合。
• Formation of a Stable 14-Helix in Short Oligomers of Furanoid <i>cis-</i>β-Sugar-Amino Acid
  作者：Srivari Chandrasekhar、Marepally Srinivasa Reddy、Bharatam Jagadeesh、Anabathula Prabhakar、Mallem H. V. Ramana Rao、Bulusu Jagannadh

  DOI：10.1021/ja0467667

  日期：2004.10.1

  Oligomers of a new class of sugar amino acids (SAA) using a xylofuranoic acid has been shown to generate a robust 14-helix. The design involved the use of xylofuranose with a cis arrangement between the amine and carboxyl groups to promote the adoption of a 14-helix instead of a mixed 12/10-helix observed in a sugar oligomer using a ribofuranoic acid and beta-Ala. The observation of a stable right-handed 14-helix in a cis-SAA is unprecedented.