2,3-O-isopropylidene-2-C-hydroxymethyl-D-ribofuranose

• 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-2-C-hydroxymethyl-D-ribofuranose
• 英文别名: 2,3-O-isopropylidene-D-hamamelose；D-hamamelose-2,3-O-acetonide；2,3-O-isopropylidine-D-hamamelose；2,3-O-Isopropyliden-D-hammamelose；(3aR,6R,6aR)-3a,6-bis(hydroxymethyl)-2,2-dimethyl-6,6a-dihydro-4H-furo[3,4-d][1,3]dioxol-4-ol
• 化学式: C₉H₁₆O₆
• 分子量: 220.222
• InChiKey: JLEGEDDIMHKLAR-PQLACBALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-O-isopropylidene-2-C-hydroxymethyl-D-ribofuranose 在 盐酸 、 4-二甲氨基吡啶 、 硫酸氢铵 、 二正丁基氧化锡 、 三乙胺 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 59.0h， 生成 Acetic acid (2R,3R,4R,5R)-4-acetoxy-3,5-bis-benzyloxymethyl-2-(6-chloro-purin-9-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Synthesis of 2-C-hydroxymethylribofuranosylpurines as potent anti-hepatitis C virus (HCV) agents

  摘要：

  On the basis of potent anti-HCV activity of 2'-C-methyladenosine, novel 2'-C-hydroxymethyladenosine analogues 2a-c were synthesized from D-ribose in order to lead to favorable interaction with HCV polymerase. Among compounds tested, adenosine derivative 2a exhibited potent anti-HCV activity, indicating that the hydroxyl group of 2'-C-hydroxymethyl substituent led to favorable interaction with HCV polymerase. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.089
• 作为产物：
  描述：

  D-核糖 在 硫酸 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 2,3-O-isopropylidene-2-C-hydroxymethyl-D-ribofuranose
  参考文献：
  名称：

  在D-核糖衍生的腈上具有高度区域选择性和非对映选择性的酸性粘土支持分子内一氧化氮-烯烃环加成反应：一种合成异硫唑啉的有效合成路线，该结构将五元和六元碳环融合。

  摘要：

  描述了从具有游离羟基的碳水化合物支架到异恶唑啉稠合碳环的有效合成途径，其具有高区域选择性和立体选择性。已经开发了D-核糖衍生的肟的蒙脱石K-10 /氯胺T氧化和原位分子内腈氧化烯-烯烃环加成（INOC），用于多样性定向合成的异恶唑啉稠合的五元和六元碳环。

  DOI：

  10.1016/j.carres.2014.06.007

文献信息

• A Versatile Total Synthesis of Trachycladines A and B and Their Analogues
  作者：Zisis V. Peitsinis、Dafni A. Melidou、John G. Stefanakis、Helen Evgenidou、Alexandros E. Koumbis

  DOI：10.1002/ejoc.201403091

  日期：2014.12

  The synthesis of marine nucleosides trachycladines A and B and two nucleoside analogues was accomplished following a versatile and high-yielding scheme starting from D-ribose. The key step involved a regio- and stereoselective direct Vorbruggen glycosylation reaction between the appropriate nucleobase and a common intermediate, 2-C-methyl-D-5-deoxyribofuranose triacetate.

  海洋核苷 trachycladines A 和 B 以及两种核苷类似物的合成是按照从 D-核糖开始的通用和高产方案完成的。关键步骤涉及适当核碱基和常见中间体 2-C-甲基-D-5-脱氧呋喃核糖三乙酸酯之间的区域选择性和立体选择性直接 Vorbruggen 糖基化反应。
• Synthesis of a ribofuranosyl cation mimic
  作者：Mikael Bols、Morten P. Persson、Waqas M. Butt、Martin Jørgensen、Peter Christensen、Lars T. Hansen

  DOI：10.1016/0040-4039(96)00202-x

  日期：1996.3

  (3S,4S)-3,4-dihydroxy-3-hydroxymethylpyrrolidine was prepared and found to be a transitionstate analogue for beta-D-ribofuranosyl cleavage.

  制备了(3S,4S)-3,4-二羟基-3-羟甲基吡咯烷，并发现其是β-D-核糖呋喃糖基裂解的过渡态类似物。
• Fragmentation of carbohydrate anomeric alkoxy radicals. A new general synthesis of cyclic ketoses
  作者：Pedro de Armas、Francisco G. Cosme、Suárez Ernesto

  DOI：10.1016/s0040-4039(00)79322-1

  日期：1993.11

  Cyclic ketones can be specifically obtained when C2 hydroxymethylated carbohydrates undergo a tandem β-fragmentation-cyclization reaction promoted by the system iodosylbenzene-iodine, under mild conditions. Pentuloses and hexuloses in furanose and pyranose form are obtained via 1,5 and 1,6 intramolecular cyclization.

  当C2羟甲基化碳水化合物在温和条件下经历由碘代苯苯碘体系促进的串联β片段化环化反应时，可以特异性地获得环酮。呋喃糖和吡喃糖形式的戊糖和己糖是通过1,5和1,6分子内环化获得的。
• 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.