(3S,4R,6S)-tetrahydro-3,4-dihydroxy-6-methyl-pyran-2-one | 13964-32-4

• 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: (3S,4R,6S)-tetrahydro-3,4-dihydroxy-6-methyl-pyran-2-one
• 英文别名: 4-deoxy-L-fucono-1,5-lactone；(3S,4R,6S)-3,4-dihydroxy-6-methyloxan-2-one
• CAS: 13964-32-4
• 化学式: C₆H₁₀O₄
• 分子量: 146.143
• InChiKey: OPHJVGRTNOTCFL-LMVFSUKVSA-N

物化性质

• 沸点：
  276.5±7.0 °C(Predicted)
• 密度：
  1.353±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

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：

  (3S,4R,6S)-tetrahydro-3,4-dihydroxy-6-methyl-pyran-2-one 在 氨 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 4,6-Didesoxy-L-xylohexonsaeureamid
  参考文献：
  名称：

  Jary,J.; Kefurt,K., Collection of Czechoslovak Chemical Communications, 1966, vol. 31, p. 2059 - 2067

  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 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 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 (3S,4R,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：——
• <scp>l</scp>-Galactose Metabolism in <i>Bacteroides vulgatus</i> from the Human Gut Microbiota
  作者：Merlin Eric Hobbs、Howard J. Williams、Brandan Hillerich、Steven C. Almo、Frank M. Raushel

  DOI：10.1021/bi500656m

  日期：2014.7.22

  A previously unknown metabolic pathway for the utilization of L-galactose was discovered in a prevalent gut bacterium, Bacteroides vulgatus. The new pathway consists of three previously uncharacterized enzymes that were found to be responsible for the conversion of L-galactose to D-tagaturonate. Bvu0219 (L-galactose dehydrogenase) was determined to oxidize L-galactose to L-galactono-1,5-lactone with k(cat) and k(cat)/K-m values of 21 s(-1) and 2.0 x 10(5) M-1 s(-1), respectively. The kinetic product of Bvu0219 is rapidly converted nonenzymatically to the thermodynamically more stable L-galactono-1,4-lactone. Bvu0220 (L-galactono-1,S-lactonase) hydrolyzes both the kinetic and thermodynamic products of Bvu0219 to L-galactonate. However, L-galactono-1,5-lactone is estimated to be hydrolyzed 300-fold faster than its thermodynamically more stable counterpart, L-galactono-1,4-lactone. In the final step of this pathway, Bvu0222 (L-galactonate dehydrogenase) oxidizes L-galactonate to D-tagaturonate with k(cat) and k(cat) /K-m values of 0.6 s(-1) and 1.7 x 10(4) M-1 s(-1), respectively. In the reverse direction, D-tagaturonate is reduced to L-galactonate with values of k(cat) and k(cat)/K-m of 90 s(-1) and 1.6 X 10(5) M-1 s(-1), respectively. D-Tagaturonate is subsequently converted to D-glyceraldehyde and pyruvate through enzymes encoded within the degradation pathway for D-glucuronate and D-galacturonate.
• Discovery of an <scp>l</scp>-Fucono-1,5-lactonase from cog3618 of the Amidohydrolase Superfamily
  作者：Merlin Eric Hobbs、Matthew Vetting、Howard J. Williams、Tamari Narindoshvili、Devon M. Kebodeaux、Brandan Hillerich、Ronald D. Seidel、Steven C. Almo、Frank M. Raushel

  DOI：10.1021/bi3015554

  日期：2013.1.8

  A member of the amidohydrolase superfamily, BmulJ_04915 from Burkholderia multivorans, of unknown function was determined to hydrolyze a series of sugar lactones: L-fiicono-1,4-lactone, n-arabino-1,4-lactone, L-xylono-1,4-lactone, D-lyxono-1,4-lactone, and L-galactono-1,4-lactone. The highest activity was shown for L-fucono-1,4-lactone with a k(cat) value of 140 s(-1) and a k(cat)/K-m value of 1.0 x 10(5) M-1 s(-1) at pH 8.3. The enzymatic product of an adjacent L-fucose dehydrogenase, BmulJ_04919, was shown to be L-fucono-1,5-lactone via nuclear magnetic resonance spectroscopy. L-Fucono-1,5-lactone is unstable and rapidly converts nonenzymatically to L-fucono-1,4-lactone. Because of the chemical instability of L-fiicono-1,5-lactone, 4-deoxy-L-fucono-1,5-lactone was enzymatically synthesized from 4-deoxy-L-fucose using L-fucose dehydrogenase. BmulJ-04915 hydrolyzed 4-deoxy-L-fucono-1,5-lactone with a k(cat) value of 990 s(-1) and a k(cat)/K-m value of 8.0 x 106 M-1 s(-1) at pH 7.1. The protein does not require divalent cations in the active site for catalytic activity. BmulJ_04915 is the second enzyme from cog3618 of the amidohydrolase superfamily that does not require a divalent metal for catalytic activity. BmulJ_04915 is the first enzyme that has been shown to catalyze the hydrolysis of either L-fucono-1,4-lactone or L-fucono-1,5-lactone. The structures of the fuconolactonase and the fucose dehydrogenase were determined by X-ray diffraction methods.
• 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.