(3R,4S,6S)-tetrahydro-3,4-dihydroxy-6-methyl-pyran-2-one | 62232-31-9

• 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,4S,6S)-tetrahydro-3,4-dihydroxy-6-methyl-pyran-2-one
• 英文别名: (3R,4S,6S)-3,4-dihydroxy-6-methyloxan-2-one
• CAS: 62232-31-9
• 化学式: C₆H₁₀O₄
• 分子量: 146.143
• InChiKey: OPHJVGRTNOTCFL-VAYJURFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 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：

  (3R,4S,6S)-tetrahydro-3,4-dihydroxy-6-methyl-pyran-2-one 在 sodium hydroxide 作用下， 生成 4,6-Didesoxy-L-arabino-hexonsaeure
  参考文献：
  名称：

  Nemec,J. et al., Collection of Czechoslovak Chemical Communications, 1968, vol. 33, p. 2097 - 2110

  摘要：

  DOI：
• 作为产物：
  描述：

  山梨酸乙酯 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 四氧化锇 、 Hydroquinone 1,4-phthalazinediyl diether 、 三苯基膦 吡啶 、 甲酸 、 甲基磺酰胺 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 三乙胺 、 potassium hexacyanoferrate(III) 作用下， 以 二氯甲烷 、 水 、 叔丁醇 、 苯 为溶剂， 反应 7.0h， 生成 (3R,4S,6S)-tetrahydro-3,4-dihydroxy-6-methyl-pyran-2-one
  参考文献：
  名称：

  De Novo Enantioselective Syntheses of Galacto-Sugars and Deoxy Sugars via the Iterative Dihydroxylation of Dienoate

  摘要：

  [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.

  DOI：

  10.1021/ol050044i

文献信息

• De novo asymmetric syntheses of C-4-substituted sugars via an iterative dihydroxylation strategy
  作者：Md. Moinuddin Ahmed、George A. O’Doherty

  DOI：10.1016/j.carres.2006.03.024

  日期：2006.7

  highly efficient route to various C-4 substituted sugar lactones has been developed. The key to the overall transformation is the sequential osmium-catalyzed dihydroxylation reaction of substituted 2,4-dienoates and an allylic substitution at the C-4 position. When the Sharpless AD-mix procedure is used in a matched sense for the second dihydroxylation reaction, it results in an exceedingly diastereo-

  已经开发了一种短且高效的途径来制备各种C-4取代的糖内酯。总体转化的关键是取代的2，4-二烯酸酯的催化的二羟基化反应和C-4位置的烯丙基取代。当将Sharpless AD-mix程序以匹配的方式用于第二个二羟基化反应时，会导致几种C-4取代糖的非对映和对映选择性合成。
• Kefurt,K. et al., Collection of Czechoslovak Chemical Communications, 1971, vol. 36, p. 124 - 131
  作者：Kefurt,K. et al.

  DOI：——

  日期：——
• 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.
• Nemec,J. et al., Collection of Czechoslovak Chemical Communications, 1968, vol. 33, p. 2097 - 2110
  作者：Nemec,J. et al.

  DOI：——

  日期：——