4(S),5(S)-dihydroxy-6(S)-methyl-tetrahydro-pyran-2-one | 476468-28-7

• 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: 4(S),5(S)-dihydroxy-6(S)-methyl-tetrahydro-pyran-2-one
• 英文别名: (4S,5S,6S)-4,5-dihydroxy-6-methyltetrahydropyran-2-one；2,6-dideoxy-L-lyxo-hexopyrano-1,5-lactone；(4S,5S,6S)-4,5-dihydroxy-6-methyloxan-2-one
• CAS: 476468-28-7
• 化学式: C₆H₁₀O₄
• 分子量: 146.143
• InChiKey: PFVBMSOEVXPQFX-RVJQKOHUSA-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：

  4(S),5(S)-dihydroxy-6(S)-methyl-tetrahydro-pyran-2-one 、 苯肼 生成 (2S,3S,4R,5S)-2,3,4,5-tetrahydroxy-N'-phenylhexanehydrazide
  参考文献：
  名称：

  SETHI, ARUN;DEEPAK, DESH;KHARE, MAHESHWARI P.;KHARE, ANAKSHI, J. NATUR. PROD., 51,(1988) N 4, C. 787-790

  摘要：

  DOI：
• 作为产物：
  描述：

  5-hydroxy-6-methyl-5,6-dihydro-2H-pyran-2-one 在 sodium tetrahydroborate 、 过氧化氢苯甲酰 、 二苯基二硒醚 、 溶剂黄146 作用下， 以 异丙醇 、 苯 为溶剂， 反应 31.0h， 生成 4(S),5(S)-dihydroxy-6(S)-methyl-tetrahydro-pyran-2-one
  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

• A first synthesis of sulfonic acid analogues of N-acetylneuraminic acid
  作者：Zoltán B. Szabó、Anikó Borbás、István Bajza、András Lipták、Sándor Antus

  DOI：10.1016/j.tetlet.2007.12.043

  日期：2008.2

  Sulfonic acid analogues of N-acetylneuraminic are synthesized from 1-thio-l-fucoside derivatives with the introduction of an azido group at C-4 of the fucose moiety and carbanionic addition onto fully protected lactones. The analogues in the form of methyl glycosides are subjected to a neuraminidase inhibition assay.

  N-乙酰神经氨酸的磺酸类似物是由1-硫-1-岩藻糖苷衍生物合成的，在岩藻糖部分的C-4处引入叠氮基，并将碳负离子加成至完全保护的内酯上。对甲基糖苷形式的类似物进行神经氨酸酶抑制测定。
• 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.
• SETHI, ARUN;DEEPAK, DESH;KHARE, MAHESHWARI P.;KHARE, ANAKSHI, J. NATUR. PROD., 51,(1988) N 4, C. 787-790
  作者：SETHI, ARUN、DEEPAK, DESH、KHARE, MAHESHWARI P.、KHARE, ANAKSHI

  DOI：——

  日期：——
• 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.