2,3-O-isopropylidene-L-apiose | 951773-88-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-O-isopropylidene-L-apiose
• 英文别名: L-apiose-2,3-O-acetonide；(3aS,6aS)-3a-(hydroxymethyl)-2,2-dimethyl-6,6a-dihydro-4H-furo[3,4-d][1,3]dioxol-6-ol
• CAS: 951773-88-9
• 化学式: C₈H₁₄O₅
• 分子量: 190.196
• InChiKey: QCNHIMWAKKHAFC-UHFKNVDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-O-isopropylidene-L-apiose 在 吡啶 、 sodium azide 、 溴 、 barium carbonate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 3-C-azidomethyl-2,3-O-isopropylidene-L-erythrono-1,4-lactone
  参考文献：
  名称：

  [EN] NOVEL IMINOSUGAR THERAPEUTICS
  [FR] NOUVEAUX AGENTS THÉRAPEUTIQUES IMINOSUCRES

  摘要：

  公开号：

  WO2011095772A3
• 作为产物：
  描述：

  2,3-异亚丙氧基-D-呋喃核糖苷 在 sodium tetrahydroborate 、 sodium periodate 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 2,3-O-isopropylidene-L-apiose
  参考文献：
  名称：

  A highly efficient synthesis of unnatural l-sugars from d-ribose

  摘要：

  A preparative and short synthesis of L-ribose and L-apiose was accomplished starting from D-ribose via stereoselective cis-dihydroxylation and C2-hydroxymethylation, respectively. These L-sugars can serve as versatile intermediates for the synthesis Of L-nucleosides. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.117

文献信息

• Synthesis and Anti-Hepatitis B Activities of 3′-Fluoro-2′-Substituted Apionucleosides
  作者：Martin Holan、Kathryn Tucker、Natalia Dyatkina、Hong Liu、April Kinkade、Guangyi Wang、Zhinan Jin、Marija Prhavc

  DOI：10.3390/molecules27082413

  日期：——

  nucleosides with novel scaffolds is of high importance. Here we report the synthesis of novel 2′-hydroxy- and 2′-hydroxymethyl-apionucleosides, 4 and 5, corresponding triphosphates and phosphoramidate prodrugs. Triphosphate 38 of 2′-hydroxymethyl-apionucleoside 5 exhibited potent inhibition of HBV polymerase with an IC50 value of 120 nM. In an HBV cell-based assay, the phosphoramidate prodrug 39 demonstrated

  核苷类似物作为抗HBV药物有很好的记录。慢性感染需要长期给药，最终导致耐药性。因此，寻找具有新型支架的核苷非常重要。在这里，我们报告了新的 2'-羟基和 2'-羟基甲基-apionucleosides、4和5、相应的三磷酸酯和氨基磷酸酯前药的合成。2'-羟甲基-apionucleoside 5 的三磷酸38表现出对 HBV 聚合酶的有效抑制作用，IC 50值为 120 nM。在基于 HBV 细胞的测定中，氨基磷酸酯前药39显示出有效的活性，EC 50值为 7.8 nM。
• Doubly carbon-branched pentoses: synthesis of both enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose using only acetonide protection
  作者：K. Victoria Booth、Sarah F. Jenkinson、Daniel Best、Fernando Fernández Nieto、Ramón J. Estévez、Mark R. Wormald、Alexander C. Weymouth-Wilson、George W.J. Fleet

  DOI：10.1016/j.tetlet.2009.06.098

  日期：2009.9

  An acetonide is the only protecting group used in the synthesis of both the enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose via the enantiomeric 3-C-methyl-L-erythronolactone [from 2-C-methyl-D-ribono-lactone or D-ribose] and 3-C-methyl-D-erythronolactone [from D-tagatose Or L-ribose]. NMR studies on unprotected C-methyl arabinoses show that methyl branching significantly affects the ratios of pyranose and furanose forms present in aqueous Solution. (C) 2009 Elsevier Ltd. All rights reserved.
• <i>C</i>-Branched Iminosugars: α-Glucosidase Inhibition by Enantiomers of isoDMDP, isoDGDP, and isoDAB–<scp>l</scp>-isoDMDP Compared to Miglitol and Miglustat
  作者：Sarah F. Jenkinson、Daniel Best、A. Waldo Saville、James Mui、R. Fernando Martínez、Shinpei Nakagawa、Takahito Kunimatsu、Dominic S. Alonzi、Terry D. Butters、Caroline Norez、Frederic Becq、Yves Blériot、Francis X. Wilson、Alexander C. Weymouth-Wilson、Atsushi Kato、George W. J. Fleet

  DOI：10.1021/jo4005487

  日期：2013.8.2

  The Ho crossed aldol condensation provides access to a series of carbon branched iminosugars as exemplified by the synthesis of enantiomeric pairs of isoDMDP, isoDGDP, and isoDAB, allowing comparison of their biological activities with three linear isomeric natural products DMDP, DGDP, and DAB and their enantiomers. L-IsoDMDP [(2S,3S,4R)-2,4-bis(hydroxymethyl)pyrrolidine-3,4-diol], prepared in 11 steps in an overall yield of 4596 from D-lyxonolactone, is a potent specific competitive inhibitor of gut disaccharidases [K-i 0.081 mu M for rat intestinal maltase] and is more effective in the suppression of hyperglycaemia in a maltose loading test than miglitol, a drug presently used in the treatment of late onset diabetes. The partial rescue of the defective F508del-CFTR function in CF-KM4 cells by L-isoDMDP is compared with miglustat and isoLAB in an approach to the treatment of cystic fibrosis.
• Cystic fibrosis and diabetes: isoLAB and isoDAB, enantiomeric carbon-branched pyrrolidine iminosugars
  作者：Daniel Best、Sarah F. Jenkinson、A. Waldo Saville、Dominic S. Alonzi、Mark R. Wormald、Terry D. Butters、Caroline Norez、Frederic Becq、Yves Blériot、Isao Adachi、Atsushi Kato、George W.J. Fleet

  DOI：10.1016/j.tetlet.2010.05.131

  日期：2010.8

  Acetonides are the only protecting groups used in the syntheses of isoDAB from D-ribose and of isoLAB from D-tagatose. isoDAB is a potent and highly specific competitive a-glucosidase inhibitor (for rice alpha-glucosidase, K(i) = 4 mu M for isoDAB compared to K(i) 14 mu M for DAB). isoDAB is not an whereas DAB is a potent inhibitor of glycogen phosphorylase. This is the first example of any potent inhibition of glycosidases by a carbon-branched iminosugar pyrrolidine. Although isoLAB shows no inhibition of any glycosidase, preliminary experiments suggest that isoLAB partially rescues the defective F508del-CFTR function and so may have a role in the study of cystic fibrosis. (C) 2010 Elsevier Ltd. All rights reserved.