(2S,3R,4R,5R)-2-(benzyloxy)-5-((R)-1,2-dihydroxyethyl)tetrahydrofuran-3,4-diol | 910647-38-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R,5R)-2-(benzyloxy)-5-((R)-1,2-dihydroxyethyl)tetrahydrofuran-3,4-diol
• 英文别名: benzyl β-D-galactofuranoside；benzyl D-galactofuranoside；benzyl-β-D-galactofuranoside；Benzyl-β-D-galactofuranosid；(2S,3R,4R,5R)-2-[(1R)-1,2-dihydroxyethyl]-5-phenylmethoxyoxolane-3,4-diol
• CAS: 910647-38-0
• 化学式: C₁₃H₁₈O₆
• 分子量: 270.282
• InChiKey: ZRYDVIBDZUMETM-NJMOYASZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5R)-2-(benzyloxy)-5-((R)-1,2-dihydroxyethyl)tetrahydrofuran-3,4-diol 在 咪唑 、 D(+)-10-樟脑磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2R,3R,4S,5R)-5-(benzyloxy)-4-(tert-butyldiphenylsilyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)tetrahydrofuran-3-ol
  参考文献：
  名称：

  Total synthesis of fuzinoside

  摘要：

  The first total syntheses of fuzinoside (1b) were achieved from o-galactose through two strategies (BCA and ABC) in 11 (total yield: 5.0%) and 15 (total yield: 3.7%) steps, respectively. Comparison of NMR data of synthetic compound 1b and those of the fuzinoside isolated from the lateral roots of Aconitum carmicaelii suggests that the structure reported in the literature(1,2) might not be accurate. The synthetic fuzinoside (1b) exhibited moderate cardiac activity in the isolated bullfrog heart assay. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.069
• 作为产物：
  描述：

  1,2,3,5,6-penta-O-benzoyl-D-galactofuranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以99%的产率得到(2S,3R,4R,5R)-2-(benzyloxy)-5-((R)-1,2-dihydroxyethyl)tetrahydrofuran-3,4-diol
  参考文献：
  名称：

  Facile synthesis of benzyl β-d-galactofuranoside. A convenient intermediate for the synthesis of d-galactofuranose-containing molecules

  摘要：

  Benzyl beta-D-galactofurano side was efficiently obtained from 1,2,3,5,6-penta-O-benzoyl-alpha, beta-D-galactofuranose, via benzyl 2,3,5,6-tetra-O-benzoyl-beta-D-galactofuranoside. Conditions for the O-debenzylation were investigated in order to evaluate the synthetic application of the benzyl group as an anomeric protector of a galactofuranose moiety in synthetic strategies involving galactofuranose. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.06.004

文献信息

• Facile Synthesis of per-<i>O-tert</i>-Butyldimethylsilyl-β-<scp>d</scp>-galactofuranose and Efficient Glycosylation via the Galactofuranosyl Iodide
  作者：Luciana Baldoni、Carla Marino

  DOI：10.1021/jo8025274

  日期：2009.3.6

  The synthesis of crystalline per-O-TBS-beta-D-galactofuranose (4 beta) as a new precursor of D-Galf units is described. Anomeric iodination by reaction with TMSI followed by in situ coupling with simple alcohols and a wide variety of glycosyl acceptors, in the absence of a promoter, was employed as a new efficient glycosylation method for the assembly Of D-galactofuranosyl moieties with high beta-stereoselectivity. Under the mild conditions of this reaction labile protective groups, like acetals, and furanosyl linkages are preserved.
• Glycofuranosides and Thioglycofuranosides. III. New Crystalline Furanosides of d-Galactose and l-Arabinose
  作者：John W. Green、Eugene Pacsu

  DOI：10.1021/ja01276a011

  日期：1938.9
• Total synthesis of fuzinoside
  作者：Ping He、Xiao-Huan Li、Qiao-Hong Chen、Jing-Song Yang、Feng-Peng Wang

  DOI：10.1016/j.tet.2014.04.069

  日期：2014.7

  The first total syntheses of fuzinoside (1b) were achieved from o-galactose through two strategies (BCA and ABC) in 11 (total yield: 5.0%) and 15 (total yield: 3.7%) steps, respectively. Comparison of NMR data of synthetic compound 1b and those of the fuzinoside isolated from the lateral roots of Aconitum carmicaelii suggests that the structure reported in the literature(1,2) might not be accurate. The synthetic fuzinoside (1b) exhibited moderate cardiac activity in the isolated bullfrog heart assay. (C) 2014 Elsevier Ltd. All rights reserved.
• Facile synthesis of benzyl β-d-galactofuranoside. A convenient intermediate for the synthesis of d-galactofuranose-containing molecules
  作者：Karina Mariño、Luciana Baldoni、Carla Marino

  DOI：10.1016/j.carres.2006.06.004

  日期：2006.9

  Benzyl beta-D-galactofurano side was efficiently obtained from 1,2,3,5,6-penta-O-benzoyl-alpha, beta-D-galactofuranose, via benzyl 2,3,5,6-tetra-O-benzoyl-beta-D-galactofuranoside. Conditions for the O-debenzylation were investigated in order to evaluate the synthetic application of the benzyl group as an anomeric protector of a galactofuranose moiety in synthetic strategies involving galactofuranose. (c) 2006 Elsevier Ltd. All rights reserved.