3-Hydroxyfurfuryl di-O-benzyl ether | 76833-05-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-Hydroxyfurfuryl di-O-benzyl ether
• 英文别名: 3-(Benzyloxy)-2-<(benzyloxy)methyl>furan；3-(Benzyloxy)-2-[(benzyloxy)methyl]furan；3-phenylmethoxy-2-(phenylmethoxymethyl)furan
• CAS: 76833-05-1
• 化学式: C₁₉H₁₈O₃
• 分子量: 294.35
• InChiKey: IIXNTCJKGNQLIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  31.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲基 3,5-二-O-苄基-D-呋喃核糖苷 在 sodium iodide 作用下， 以 吡啶 、 六甲基磷酰三胺 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 50.0h， 生成 3-Hydroxyfurfuryl di-O-benzyl ether
  参考文献：
  名称：

  Facile synthesis of 2-deoxy-2-substituted D-arabinofuranose derivatives

  摘要：

  DOI：

  10.1021/jo00322a007

文献信息

• Furanosyl Oxocarbenium Ion Conformational Energy Landscape Maps as a Tool to Study the Glycosylation Stereoselectivity of 2‐Azidofuranoses, 2‐Fluorofuranoses and Methyl Furanosyl Uronates
  作者：Stefan van der Vorm、Thomas Hansen、Erwin R. van Rijssel、Rolf Dekkers、Jerre M. Madern、Herman S. Overkleeft、Dmitri V. Filippov、Gijsbert A. van der Marel、Jeroen D. C. Codée

  DOI：10.1002/chem.201900651

  日期：2019.5.23

  reactive intermediates is dictated by the conformation of these species. The nature and configuration of functional groups on the carbohydrate ring affect the stability of glycosyl oxocarbenium ions and control the overall shape of the cations. We herein map the stereoelectronic substituent effects of the C2‐azide, C2‐fluoride and C4‐carboxylic acid ester on the stability and reactivity of the complete

  糖基氧碳鎓离子的3D形状决定了它们的稳定性和反应性，在这些反应性中间体上发生的S N 1反应的立体化学过程取决于这些物质的构象。碳水化合物环上官能团的性质和构型影响糖基氧碳鎓离子的稳定性，并控制阳离子的整体形状。我们在本文中通过组合计算和实验方法，绘制了C2-叠氮化物，C2-氟化物和C4-羧酸酯的立体电子取代基对整套非对映异构呋喃糖酶的稳定性和反应性的影响。出乎意料的是，所有研究的呋喃糖基供体都以高度立体选择性的方式反应，从而生成1,2-顺式产品，木糖系列反应除外。核糖，阿拉伯糖和lyxo构成的呋喃糖苷的1,2-顺式选择性可以追溯到中间氧碳鎓离子的最低能量3 E或E 3构象异构体。对木糖基供体的选择性缺乏与采用其他构象的氧碳鎓离子的出现有关。
• A synthesis of 9-(2-deoxy-2-fluoro-.beta.-D-arabinofuranosyl)adenine and -hypoxanthine. An effect of C3'-endo to C2'-endo conformational shift on the reaction course of 2'-hydroxyl group with DAST
  作者：Krzysztof W. Pankiewicz、Jacek Krzeminski、Lech A. Ciszewski、Wu Yon Ren、Kyoichi A. Watanabe

  DOI：10.1021/jo00028a030

  日期：1992.1

  O3',O5',N6-Tritrityladenosine (6), 3',5'-di-O-trityl-N1-benzylinosine (15), and 3',5'-di-O-tritylinosine (18) were prepared and subjected to nucleophilic reaction with DAST. Thus, 6 afforded 2'-beta-fluorine-substituted nucleoside 11 along with the isomeric 2-deoxy-2-(N-trityladenin-3-yl)-3,5-di-O-trityl-alpha-D-arabinofuranosyl fluoride (12). Nucleoside 15, under the same treatment with DAST, gave the desired 2'-fluoroarabino derivative 16 exclusively in high yield. Although 18 was converted into the 2'-beta-fluoro product 19 under the similar conditions, the yield was low. A plausible mechanism of formation of 12 is discussed. Deprotection of 11 and 16 afforded the desired 9-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)adenine (1) and -hypoxanthine (2), respectively, in high yield. The conformational influence of sugar protecting groups on the rate of nucleophilic substitution against elimination is discussed. Treatment of O3',O5',N1-benzylinosine (20) with DAST afforded only the elimination products 9-(3',5'-di-O-benzyl-beta-D-erythro-pent-2-enofuranosyl)-1-benzylhypoxanthine (22) and 3-(benzyloxy)-2-[(benzyloxy)methyl]furan (23). On the other hand, 9-(3,5-di-O-trityl-beta-D-arabinofuranosyl)adenine (26) (prepared from 6 by triflyation followed by NaOAc treatment and deacetylation) afforded a mixture from which 2'-deoxy-2'-fluoroadenosine (27) and 9-(2-deoxy-3,5-di-O-trityl-D-erythro-pent-1-enofuranosyl)-N6-trityladenine (28) were isolated in 60 and 30% yield, respectively. O2',O5',N6-Tritrityladenosine (7) was selectively detritylated with HCO2H/Et2O to give O2',N6-ditrityladenosine (30), which, upon treatment with benzyl chloride/KOH, afforded 3',5'-di-O-benzyl-O2',N6-ditrityladenosine (31). 9-(3,5-Di-O-benzyl-beta-D-arabinofuranosyl)adenine (35) was prepared from 31 by further detritylation with CF3CO2H/CHCl3 and triflyation followed by NaOAc treatment and deacetylation of the product. Treatment of 35 with DAST followed by hydrogenolytic debenzylation afforded 2'-deoxy-2'-fluoroadenosine (3) in high yield. The three-step synthesis described herein, albeit about 10% overall yield, is far superior to the currently available multistep procedures which give the desired 2'-fluoroarabinosylpurines in much less overall yields.
• KRZEMINSKI, JACEK;NAWROT, BARBARA;PANKIEWICZ, KRZYSZTOF W.;WATANABE, KYOI+, NUCLEOSIDES AND NUCLEOTIDES, 10,(1991) N, C. 781-798
  作者：KRZEMINSKI, JACEK、NAWROT, BARBARA、PANKIEWICZ, KRZYSZTOF W.、WATANABE, KYOI+

  DOI：——

  日期：——
• Facile synthesis of 2-deoxy-2-substituted D-arabinofuranose derivatives
  作者：Tsann-Long Su、Robert S. Klein、Jack J. Fox

  DOI：10.1021/jo00322a007

  日期：1981.4