(2R,3S,6R)-2-(hydroxymethyl)-6-(4-methoxyphenoxy)-3,6-dihydro-2H-pyran-3-ol | 197449-36-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,3S,6R)-2-(hydroxymethyl)-6-(4-methoxyphenoxy)-3,6-dihydro-2H-pyran-3-ol
• 英文别名: p-methoxyphenyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• CAS: 197449-36-8
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: WJNQUQYMMGPXIT-XQQFMLRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S,6R)-2-(hydroxymethyl)-6-(4-methoxyphenoxy)-3,6-dihydro-2H-pyran-3-ol 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 以54%的产率得到(2R,6R)-6-(hydroxymethyl)-2-(4-methoxyphenoxy)-2H-pyran-5-one
  参考文献：
  名称：

  2,3-Dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents: Design, synthesis, biological evaluation and SAR studies

  摘要：

  The alarming resurgence of tuberculosis (TB) underlines the urgent need for development of new and potent anti-TB drugs. Towards this goal we herein report the design and synthesis of 2,3-dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents. These easily accessible, small molecules were found to exhibit in vitro activity against Mycobacterium tuberculosis H37Rv in a MIC range of 0.78 mu g/mL to 25 mu g/mL. A detailed SAR study on these hex-2-enopyranosid-4-uloses led to the identification of compound 5g (5007-724) which on the basis of low MIC (0.78 mu g/mL-M. tuberculosis H37Rv; 1.56 mu g/mL-MDR, SDR strains of M. tuberculosis; 0.78 mu g/mL-inhibition of intracellular replication of M. tuberculosis) and SI value of 13.5 has been identified as a promising lead molecule. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.002
• 作为产物：
  描述：

  4-甲氧基苯酚 在 甲醇 、 碘 、 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,3S,6R)-2-(hydroxymethyl)-6-(4-methoxyphenoxy)-3,6-dihydro-2H-pyran-3-ol
  参考文献：
  名称：

  2,3-Dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents: Design, synthesis, biological evaluation and SAR studies

  摘要：

  The alarming resurgence of tuberculosis (TB) underlines the urgent need for development of new and potent anti-TB drugs. Towards this goal we herein report the design and synthesis of 2,3-dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents. These easily accessible, small molecules were found to exhibit in vitro activity against Mycobacterium tuberculosis H37Rv in a MIC range of 0.78 mu g/mL to 25 mu g/mL. A detailed SAR study on these hex-2-enopyranosid-4-uloses led to the identification of compound 5g (5007-724) which on the basis of low MIC (0.78 mu g/mL-M. tuberculosis H37Rv; 1.56 mu g/mL-MDR, SDR strains of M. tuberculosis; 0.78 mu g/mL-inhibition of intracellular replication of M. tuberculosis) and SI value of 13.5 has been identified as a promising lead molecule. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.002

文献信息

• Pd-Catalyzed Umpolung Chemistry of Glycal Acetates and Their [2,3]-Dehydrosugar Isomers
  作者：Juyeol Lee、Young Ho Rhee

  DOI：10.1021/acs.orglett.1c04004

  日期：2022.1.21

  Glycals and their [2,3]-dehydrosugar derivatives have commonly been used in synthetic chemistry as electrophiles. Here we report a Pd-catalyzed polar inversion (umpolung) of this reaction, where the glycals and isomers can be used as nucleophiles. The reaction showed high regio- and stereoselectivity in the presence of numerous aromatic and aliphatic aldehydes. The synthetic utility of this reaction

  Glycals 和它们的 [2,3]-脱氢糖衍生物通常在合成化学中用作亲电子试剂。在这里，我们报告了该反应的 Pd 催化的极性反转（umpolung），其中糖基和异构体可用作亲核试剂。在大量芳香族和脂肪族醛的存在下，该反应显示出高区域选择性和立体选择性。该反应的合成效用通过抗癌天然产物粘液素的四氢吡喃片段的短合成得到证明。
• Effective and chemoselective glycosylations using 2,3-unsaturated sugars
  作者：Shunichi Kusumi、Kaname Sasaki、Sainan Wang、Tatsuya Watanabe、Daisuke Takahashi、Kazunobu Toshima

  DOI：10.1039/c004204h

  日期：——

  Glycosyl donors containing a double bond between C2 and C3 were designed by mimicking the reaction mechanism of lysozyme-initiated hydrolysis of mucopolysaccharides. It was found that, under various glycosylation conditions, the reactivities of 2,3-unsaturated glycosyl acetates were significantly higher, while those of the corresponding 2,3-unsaturated-4-keto glycosyl acetates were much lower than

  糖基通过模拟溶菌酶引发的粘多糖水解的反应机理，设计了在C2和C3之间含有双键的供体。结果发现，在各种糖基化条件下，2,3-不饱和乙酸糖基乙酸酯的反应性显着较高，而相应的2,3-不饱和-4-酮糖基乙酸酯的反应性则大大低于相应的2,3-不饱和-4-酮糖基乙酸酯。2,3-二脱氧（2，3-饱和的）乙酸糖基酯。基于这些结果，化学选择性糖基化进行了有效地实现通过组合技术中使用三种类型的短步骤糖基供体构建几种类型的脱氧寡糖。此外，发现高反应性的2，3-不饱和乙酸糖基酯可用于合成低反应性叔醇的O-糖苷。
• A Chemo-Enzymatic Synthesis of D-Allosamine Derivatives from Tri-<i>O</i>-acetyl-D-glucal
  作者：Takeshi Sugai、Hanako Okazaki、Atsuhito Kuboki、Hiromichi Ohta

  DOI：10.1246/bcsj.70.2535

  日期：1997.10

  N-Acetyl-D-allosamine and its derivatives were synthesized from tri-O-acetyl-D-glucal based on lipase-catalyzed selective protection of primary alcohols, [3,3] sigmatropic rearrangement of allylic trichloroacetimidates, and stereoselective ruthenium-catalyzed dihydroxylation. In the course of this study, it was revealed that the Pseudomonas lipase-catalyzed acetylation occurred in a high yield (> 90%)

  基于脂肪酶催化的伯醇选择性保护、烯丙基三氯乙酰亚胺酯的 [3,3] σ 重排和立体选择性钌催化的二羟基化，由三-O-乙酰基-D-葡糖合成 N-乙酰基-D-阿洛胺及其衍生物. 在这项研究过程中，发现假单胞菌脂肪酶催化的乙酰化以高产率 (> 90%) 发生，仅发生在源自三-O-乙酰基-D-glucal 的三种费里尔重排产物的伯醇上。
• A new route toward 2-acetamido-4-O-methyl-2-deoxy-d-mannopyranose from a Ferrier derivative of tri-O-acetyl-d-glucal, which contributes to aldolase-catalyzed synthesis of laninamivir (CS-8958)
  作者：Hayato Okazaki、Kengo Hanaya、Mitsuru Shoji、Noriyasu Hada、Takeshi Sugai

  DOI：10.1016/j.tet.2013.07.018

  日期：2013.9

  was the starting material, and it was derived via Ferrier reaction from tri-O-acetyl-d-glucal. The total yield was 43% over six steps from the starting material. As the key steps, Payne oxidation provided a syn-epoxy alcohol, and the inversion from an aziridine to an oxazoline proceeded stereoselectively. Although the ring opening reaction of the epoxide with an azide gave both the 2- and 3-azido regioisomers

  朝向2-乙酰氨基-4-甲新路线ö -2-脱氧-甲基d -mannopyranose（4- Ò -methylManNAc），7-化学-酶促前体ö -methylsialic酸和拉尼米韦，建立了。已知的p -甲氧基苯基6- ø - （叔丁基二甲基硅烷基）-2,3-二脱氧α- d -赤-己-2-烯吡喃糖苷为起始原料，和它是通过从三Ferrier的反应衍生ö乙酰基d-葡萄糖醛。从起始原料开始的六个步骤的总产率为43％。作为关键步骤，佩恩氧化提供了一种合成-环氧醇，并且从氮丙啶转化为恶唑啉是立体选择性地进行的。尽管环氧化物与叠氮化物的开环反应给出了2-和3-叠氮基区域异构体，但是它们可以通过独立的途径合并成所需的氮丙啶。