methyl 3-azido-3-deoxy-1,2-O-(1-methylethylidne)-α-D-xylofuranoate | 1060716-74-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-azido-3-deoxy-1,2-O-(1-methylethylidne)-α-D-xylofuranoate
• 英文别名: methyl (3aR,5S,6R,6aR)-6-azido-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carboxylate
• CAS: 1060716-74-6
• 化学式: C₉H₁₃N₃O₅
• 分子量: 243.219
• InChiKey: PJJDNSSWKNKOBA-LZCNBPATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3-azido-3-deoxy-1,2-O-(1-methylethylidne)-α-D-xylofuranoate 在 palladium on activated charcoal 氢气 、 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 、 乙酸乙酯 为溶剂， 生成
  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-glucofuranose 在 sodium dihydrogenphosphate sodium chlorite 、 sodium periodate 、 双氧水 作用下， 以 乙醚 、 乙腈 为溶剂， 生成 methyl 3-azido-3-deoxy-1,2-O-(1-methylethylidne)-α-D-xylofuranoate
  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

• Simultaneous Parallel and Antiparallel Self-Assembly in a Triazole/Amide Macrocycle Conformationally Homologous to <scp>d</scp>-,<scp>l</scp>-α-Amino Acid Based Cyclic Peptides: NMR and Molecular Modeling Study
  作者：Abhijit Ghorai、Anindita Gayen、Goutam Kulsi、E. Padmanaban、Aparna Laskar、Basudeb Achari、Chaitali Mukhopadhyay、Partha Chattopadhyay

  DOI：10.1021/ol2022356

  日期：2011.10.21

  macrocycle, synthesized from a triazole amide oligomer of cis-furanoid sugar triazole amino acids, possesses a conformation resembling the d-,l-α-amino acid based cyclic peptides despite having uniform backbone chirality. It undergoes a unique mode of self-assembly through an antiparallel backbone to backbone intermolecular H-bonding involving amide NH and triazole N2/N3 as well as parallel stacking

  由顺式呋喃糖三唑氨基酸的三唑酰胺低聚物合成的1,4-连接的三唑/酰胺基拟肽大环化合物，尽管具有一致的骨架手性，但其结构类似于d-，1 -α-氨基酸基环状肽。 。它通过反平行骨架与骨架间分子间的氢键结合（包括酰胺NH和三唑N2 / N3）以及通过酰胺NH和羰基氧的氢键平行堆叠而经历了独特的自组装模式，从而形成了管状纳米结构。
• Phosphine-mediated cascade reaction of azides with MBH-acetates of acetylenic aldehydes to substituted pyrroles: a facile access to N-fused pyrrolo-heterocycles
  作者：Chada Raji Reddy、Motatipally Damoder Reddy、Boinapally Srikanth

  DOI：10.1039/c2ob25272d

  日期：——

  One-pot synthesis of substituted pyrroles by a cascade reaction of azides with Morita–Baylis–Hillman acetates of acetylenic aldehydes is described and the reaction is efficiently mediated by triphenyl phosphine at room temperature. Sodium azide is successfully used to provide N-unsubstituted pyrroles, while alkyl azides afforded the corresponding N-alkylated pyrroles through a sequence of allylic substitution/azide

  描述了叠氮化物与炔属醛的森田-贝利斯-希尔曼乙酸盐的级联反应的一锅法合成取代的吡咯，该反应在室温下由三苯基膦有效地介导。叠氮化钠已成功用于提供N-未取代的吡咯，而烷基叠氮化物通过一系列烯丙基取代/叠氮化物还原/环异构化反应提供了相应的N-烷基化吡咯。所获得的产品为吲哚并吲哚，吡咯并异喹啉和8-氧代-5、6、7、8-四氢吲哚并嗪提供了新的入口。
• 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。