(4R,5R,6S)-4,5-二羟基-6-甲基四氢-2H-吡喃-2-酮 | 476468-27-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: (4R,5R,6S)-4,5-二羟基-6-甲基四氢-2H-吡喃-2-酮
• 英文名称: 4(R),5(R)-dihydroxy-6(S)-methyl-tetrahydro-pyran-2-one
• 英文别名: (4R,5R,6S)-4,5-dihydroxy-6-methyltetrahydropyran-2-one；(4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-one
• CAS: 476468-27-6
• 化学式: C₆H₁₀O₄
• 分子量: 146.143
• InChiKey: PFVBMSOEVXPQFX-RPDRRWSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5R,6S)-4,5-二羟基-6-甲基四氢-2H-吡喃-2-酮 在 sodium cyanoborohydride 作用下， 生成 L-digitoxose
  参考文献：
  名称：

  A systematic strategy for preparation of uncommon sugars through enzymatic resolution and ring-closing metathesis

  摘要：

  A systematic synthetic strategy has been developed for producing uncommon sugars. This method involved kinetic resolution allylic alcohol followed by ring-closing-metathesis (RCM) to generate optical pure lactones as the common precursors. After further derivatization, four representative uncommon sugar units were successfully synthesized. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.014
• 作为产物：
  描述：

  rel-(5R,6S)-5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 在 吡啶 、 sodium hypochlorite 、 sodium tetrahydroborate 、 二苯基二硒醚 、 溶剂黄146 作用下， 以 异丙醇 为溶剂， 反应 2.0h， 生成 (4R,5R,6S)-4,5-二羟基-6-甲基四氢-2H-吡喃-2-酮
  参考文献：
  名称：

  A divergent strategy for constructing a sugar library containing 2,6-dideoxy sugars and uncommon sugars with 4-substitution

  摘要：

  A practical strategy has been developed for delivering 2,6-dideoxy sugars and uncommon sugars with 4-substitution. This strategy employed Ferrier rearrangement reaction and BF3 center dot OEt2-induced peroxidation to construct key intermediates 2,3-unsaturated glycosides and alpha,beta-unsaturated lactones from peracetyl rhamnal. After further derivatization, four uncommon sugars with 4-substitution and eight uncommon sugar units with 3,4-disubstitution were successfully synthesized. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.019

文献信息

• Synthesis of 2,6-Dideoxysugars via Ring-Closing Olefinic Metathesis
  作者：Peter R. Andreana、Jason S. McLellan、Yongchen Chen、Peng George Wang

  DOI：10.1021/ol026710m

  日期：2002.10.1

  graphicGrubbs' RuCl2(=CHPh)(PCy3)(2) (catalyst 1) and RuCl2(=CHPh)(PCy3)(IMess) (catalyst 2) complexes have been successfully utilized in the construction of beta,gamma-unsaturated delta-lactones containing various substitution patterns of methyl groups. Asymmetric dihydroxylation followed by reduction leads to 3,4-cis-dihydroxy-2,6-dideoxypyranoses, which have proven to play very important biological roles as key components of natural products.
• A systematic strategy for preparation of uncommon sugars through enzymatic resolution and ring-closing metathesis
  作者：Lizhi Zhu、James P. Kedenburg、Ming Xian、Peng George Wang

  DOI：10.1016/j.tetlet.2004.12.014

  日期：2005.1

  A systematic synthetic strategy has been developed for producing uncommon sugars. This method involved kinetic resolution allylic alcohol followed by ring-closing-metathesis (RCM) to generate optical pure lactones as the common precursors. After further derivatization, four representative uncommon sugar units were successfully synthesized. (C) 2004 Elsevier Ltd. All rights reserved.
• A divergent strategy for constructing a sugar library containing 2,6-dideoxy sugars and uncommon sugars with 4-substitution
  作者：Guisheng Zhang、Lei Shi、Qingfeng Liu、Jingmei Wang、Lu Li、Xiaobing Liu

  DOI：10.1016/j.tet.2007.07.019

  日期：2007.9

  A practical strategy has been developed for delivering 2,6-dideoxy sugars and uncommon sugars with 4-substitution. This strategy employed Ferrier rearrangement reaction and BF3 center dot OEt2-induced peroxidation to construct key intermediates 2,3-unsaturated glycosides and alpha,beta-unsaturated lactones from peracetyl rhamnal. After further derivatization, four uncommon sugars with 4-substitution and eight uncommon sugar units with 3,4-disubstitution were successfully synthesized. (c) 2007 Elsevier Ltd. All rights reserved.