(+/-)-(3R,4R,5S,1'R)-dihydro-3,4-dihyroxy-5-(1'-hydroxyethyl)furan-2(3H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (+/-)-(3R,4R,5S,1'R)-dihydro-3,4-dihyroxy-5-(1'-hydroxyethyl)furan-2(3H)-one
• 英文别名: D-Fucono-1,4-lactone；(3R,4R,5S)-3,4-dihydroxy-5-[(1R)-1-hydroxyethyl]oxolan-2-one
• 化学式: C₆H₁₀O₅
• 分子量: 162.142
• InChiKey: VASLEPDZAKCNJX-AIHAYLRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-(3R,4R,5S,1'R)-dihydro-3,4-dihyroxy-5-(1'-hydroxyethyl)furan-2(3H)-one 在 正丁基锂 、 三氟甲磺酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 25.0h， 生成
  参考文献：
  名称：

  Stereoselective C-glycosidation of d-fucose derivatives directed by the protective groups

  摘要：

  Stereoselectivity in the C-glycosidation of lactones derived from D-fucose by following Kishi's method, which involves the addition of a nucleophile onto a carbohydrate-derived lactone and subsequent reduction of the lactol, was found to be reliant on the nature of the C2 and C3 protective groups. Lactones bearing TBDMS protecting groups selectively afford 1,3-trans products (alpha anomer), in which the stereoselective outcome is in apparent concordance with Woerpel's model. On the other hand, their benzylated congeners produce the 1,3-cis products (beta anomer) as the major diastereoisomers. The latter results suggest an abnormal behavior during the stereoselective nucleophilic substitution at the anomeric position of the benzylated lactones. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.04.005
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 水 作用下， 生成 (+/-)-(3R,4R,5S,1'R)-dihydro-3,4-dihyroxy-5-(1'-hydroxyethyl)furan-2(3H)-one
  参考文献：
  名称：

  Votocek, vol. 27, p. 18

  摘要：

  DOI：

文献信息

• De Novo Enantioselective Syntheses of <i>Galacto</i>-Sugars and Deoxy Sugars via the Iterative Dihydroxylation of Dienoate
  作者：Md. Moinuddin Ahmed、Bryan P. Berry、Thomas J. Hunter、Dennis J. Tomcik、George A. O'Doherty

  DOI：10.1021/ol050044i

  日期：2005.2.1

  [GRAPHICS]An efficient route to various sugar lactones has been developed. Key to the overall transformation is the sequential osmium-catalyzed dihydroxylation of 2,4-dienoates. The simplest (one-step/racemic) example of this reaction occurs when the dihydroxylation is performed with aqueous NMO in MeOH. When the first dihydroxylation is performed using the AD-mix procedure, an enantioselective variant results. When a matched AD-mix procedure is used for the second dihydroxylation, an exceedingly diastereo- and enantioselective synthesis of galacto-1,4-lactone results.
• Votocek, vol. 27, p. 18
  作者：Votocek

  DOI：——

  日期：——
• Votocek, Chemische Berichte, 1910, vol. 43, p. 480
  作者：Votocek

  DOI：——

  日期：——
• Stereoselective C-glycosidation of d-fucose derivatives directed by the protective groups
  作者：Omar Cortezano-Arellano、Camilo A. Meléndez-Becerra、Fernando Cortés、Fernando Sartillo-Piscil、Alejandro Cordero-Vargas

  DOI：10.1016/j.carres.2014.04.005

  日期：2014.7

  Stereoselectivity in the C-glycosidation of lactones derived from D-fucose by following Kishi's method, which involves the addition of a nucleophile onto a carbohydrate-derived lactone and subsequent reduction of the lactol, was found to be reliant on the nature of the C2 and C3 protective groups. Lactones bearing TBDMS protecting groups selectively afford 1,3-trans products (alpha anomer), in which the stereoselective outcome is in apparent concordance with Woerpel's model. On the other hand, their benzylated congeners produce the 1,3-cis products (beta anomer) as the major diastereoisomers. The latter results suggest an abnormal behavior during the stereoselective nucleophilic substitution at the anomeric position of the benzylated lactones. (C) 2014 Elsevier Ltd. All rights reserved.