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.
• A highly efficient synthesis of unnatural l-sugars from d-ribose
  作者：Mikyung Yun、Hyung Ryong Moon、Hea Ok Kim、Won Jun Choi、Yong-Chul Kim、Chul-Seung Park、Lak Shin Jeong

  DOI：10.1016/j.tetlet.2005.06.117

  日期：2005.8

  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.
• 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.
• [EN] NOVEL IMINOSUGAR THERAPEUTICS<br/>[FR] NOUVEAUX AGENTS THÉRAPEUTIQUES IMINOSUCRES
  申请人：SUMMIT CORP PLC

  公开号：WO2011095772A3

  公开（公告）日：2011-10-20