(2S, 6R)-6-hydroxy-2-methyl-2H-pyran-3(6H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2S, 6R)-6-hydroxy-2-methyl-2H-pyran-3(6H)-one
• 英文别名: (2R,6S)-2-hydroxy-6-methyl-2H-pyran-5-one
• 化学式: C₆H₈O₃
• 分子量: 128.128
• InChiKey: PLYSJDAYJMFETG-UJURSFKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S, 6R)-6-hydroxy-2-methyl-2H-pyran-3(6H)-one 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 四氧化锇 、 cerium(III) chloride 、 二正丁基氧化锡 、 N-甲基吗啉氧化物 、 三苯基膦 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 22.17h， 生成 [(2S,3S,4S,5R,6S)-6-[[(3aR,4R,6S,7S,7aR)-4-dodecoxy-2,2,6-trimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]oxy]-5-hydroxy-2-methyl-4-[[(2R,6S)-6-methyl-5-oxo-2H-pyran-2-yl]oxy]oxan-3-yl] acetate
  参考文献：
  名称：

  Structure–Activity Relationship Study of the Cleistriosides and Cleistetrosides for Antibacterial/Anticancer Activity

  摘要：

  Two known cleistriosides and six known cleistetrosides were synthesized and evaluated for anticancer and antibacterial activities. This study, for the first time, reports anticancer activity and comprehensively the antibacterial activity for these oligosaccharide natural products. In addition, two new unnatural cleistetroside analogues were synthesized and tested. Biological activities for the 10 oligosaccharides against B. subtilis were found to range between 4 and >64 mu M and for NCI-H460 human lung cancer epithelial cells between 7.5 and 90.9 mu M. Similar activities were found for seven of the oligosaccharides against the NCI panel of 60 cell lines. The degree of acylation and location of the specific acetate groups had significant effects on the anticancer and antibacterial activity of both the cleistriosides and the cleistetrosides.

  DOI：

  10.1021/ml300303g
• 作为产物：
  描述：

  (S)-1-(2-furanyl)ethanol 在 N-溴代丁二酰亚胺(NBS) 、 sodium acetate 、 碳酸氢钠 作用下， 以 氘代四氢呋喃 、 水 为溶剂， 反应 1.0h， 生成 (2S, 6R)-6-hydroxy-2-methyl-2H-pyran-3(6H)-one
  参考文献：
  名称：

  洋地黄毒苷α-L-/α-D-糖苷的C3'/ C4'-立体化学作用对癌细胞的细胞毒性作用

  摘要：

  Sweet'n低立体声：使用沃顿反应以及非对映选择性的钯催化的糖基化和其他糖基化后的转化来合成洋地黄毒苷类似物。针对一组癌细胞系的细胞毒性评估揭示了洋地黄毒苷单糖中C3'/ C4'-羟基官能团的立体化学和取代极限。

  DOI：

  10.1002/cmdc.201200465

文献信息

• Total Synthesis of (−)-Angiopterlactone B
  作者：Marie I. Thomson、Gary S. Nichol、Andrew L. Lawrence

  DOI：10.1021/acs.orglett.7b00929

  日期：2017.5.5

  An enantioselective total synthesis of (−)-angiopterlactone B has been accomplished in four steps. The synthesis features a proposed biomimetic domino ring-contraction/oxa-Michael/Michael dimerization sequence, forming three new bonds, two new rings, and three new contiguous stereogenic centers in a single step. It has been determined that the originally proposed absolute configuration of natural

  （-）-血管内酯B的对映选择性全合成已通过四个步骤完成。该合成具有拟议的仿生多米诺环收缩/ oxa-Michael / Michael二聚序列，可在一个步骤中形成三个新键，两个新环和三个新的连续立体中心。已经确定天然（+）-血管翅内酯B的最初提出的绝对构型需要修改。这表明已知的糖苷天然产物angiopteroside是（+）-angiopterlactone B的可能的生物合成前体。
• De novo asymmetric synthesis and biological analysis of the daumone pheromones in Caenorhabditis elegans and in the soybean cyst nematode Heterodera glycines
  作者：Haibing Guo、James J. La Clair、Edward P. Masler、George A. O'Doherty、Yalan Xing

  DOI：10.1016/j.tet.2016.03.033

  日期：2016.5

  The de novo asymmetric total syntheses of daumone 1, daumone 3 along with 5 new analogs are described. The key steps of our approach are: the diastereoselective palladium catalyzed glycosylation reaction; the Noyori reduction of 2-acetylfuran and an ynone, which introduce the absolute stereochemistry of the sugar and aglycon portion of daumone; and an Achmatowicz rearrangement, an epoxidation and a

  描述了daumone 1，daumone 3以及5种新类似物的从头不对称总合成。我们方法的关键步骤是：非对映选择性钯催化的糖基化反应；2-乙酰呋喃和炔酮的诺约还原，引入了决明的糖和糖苷配基部分的绝对立体化学；然后进行Achmatowicz重排，环氧化和开环，以确保Daumone的其余不对称性。评估了合成的菊粉1和3以及相关类似物在秀丽隐杆线虫中的dauer活性以及对相关线虫H.甘氨酸孵化的影响。该数据提供了额外的结构活性关系（SAR），可进一步指导线虫信号的研究。
• Short and Efficient Synthetic Route to Methyl α-Trioxacarcinoside B and Anomerically Activated Derivatives
  作者：Thomas Magauer、Andrew G. Myers

  DOI：10.1021/ol202315m

  日期：2011.10.21

  A 9-step synthetic route to the complex carbohydrate methyl α-trioxacarcinoside B from 2-acetylfuran is described. Anomerically activated forms, including 1-phenylthio, 1-O-(4′-pentenyl), 1-fluoro, and 1-O-acetyl derivatives are also prepared.

  描述了从 2-乙酰呋喃合成复杂碳水化合物甲基 α-trioxacarcinoside B 的 9 步合成路线。还制备了异头活化形式，包括 1-苯硫基、1- O- (4'-戊烯基)、1-氟和 1- O-乙酰基衍生物。
• Synthesis of Several Cleistrioside and Cleistetroside Natural Products via a Divergent De Novo Asymmetric Approach
  作者：Bulan Wu、Miaosheng Li、George A. O’Doherty

  DOI：10.1021/ol1023344

  日期：2010.12.3

  The de novo asymmetric syntheses of several partially acylated dodecanyl tri- and tetra-rhamnoside natural products (cleistriosides-5 and 6 and cleistetrosides-2 to 7) have been achieved (19−24 steps). The divergent route requires the use of three or less protecting groups. The asymmetry was derived via Noyori reduction of an acylfuran. The rhamno-stereochemistry was installed by a diastereoselective

  已经实现了几种部分酰化的十二烷基三和四鼠李糖苷天然产物（cleistriosides- 5和6和 cleistetrosides- 2至7）的从头不对称合成（19-24 步）。不同的路线需要使用三个或更少的保护基团。不对称性是通过酰基呋喃的 Noyori 还原得出的。通过非对映选择性钯催化的糖基化、酮还原和二羟基化来安装鼠李糖立体化学。
• <i>De Novo</i> Asymmetric Synthesis of All-<scp>d</scp>-, All-<scp>l</scp>-, and <scp>d</scp>-/<scp>l</scp>-Oligosaccharides Using Atom-less Protecting Groups
  作者：Ravula Satheesh Babu、Qian Chen、Sang-Woo Kang、Maoquan Zhou、George A. O’Doherty

  DOI：10.1021/ja305321e

  日期：2012.7.25

  and C-O π-bond functionality, as atom-less protecting groups as well as an anomeric directing group (via a Pd-π-allyl), highlights the atom-economical aspects of the route to a divergent set of natural and unnatural oligosaccharides (i.e., various d-/l-diastereomers of oligosaccharides as well as deoxysugars which lack C-2 anomeric directing groups). For example, in only 12 steps, the construction of

  由于需要多个步骤以及许多选择性保护和脱保护，寡糖合成受到阻碍。在此，我们报告了一种用于生物和药物结构活性研究的各种寡糖基序的高效从头途径。整体效率的关键是明智地使用不对称催化和合成设计。这些绿色原则包括双向使用高度立体选择性催化（Pd（0）催化的糖基化/后糖基化）。此外，CC 和 CO π 键官能团的化学选择性使用，作为无原子保护基团以及异头导向基团（通过 Pd-π-烯丙基），突出了通往发散路线的原子经济方面一组天然和非天然寡糖（即，低聚糖的各种 d-/l-非对映异构体以及缺乏 C-2 异头导向基团的脱氧糖）。例如，仅用 12 个步骤，就从非手性酰基呋喃构建了具有 35 个立体中心的高度支化七糖。