4-hydroxy-6-methyl-3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2-pyrone | 590410-78-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxy-6-methyl-3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2-pyrone
• 英文别名: 4-hydroxy-6-methyl-3-[(2S,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]pyran-2-one
• CAS: 590410-78-9
• 化学式: C₄₀H₄₀O₈
• 分子量: 648.753
• InChiKey: BREDCVSYAYZDBW-DOWKINRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  48
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-hydroxy-6-methyl-3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2-pyrone 在 palladium dihydroxide 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以65%的产率得到C³-β-D-galactopyranosyl-4-hydroxy-2-pyrone
  参考文献：
  名称：

  Synthetic Studies Directed toward the Assembly of the C-Glycoside Fragment of the Telomerase Inhibitor D8646-2-6

  摘要：

  GraphicsConstruction and characterization of the C-glycosidic moiety of telomerase inhibitor D8646-2-6 (1) are described. This is the first example of the C-glycosylation using electron-poor aromatics, 4-hydroxypyrone, as a glycosyl acceptor. The glycosylation reaction and base-promoted isomerization affords desired beta-C-glycoside in a 61% overall yield.

  DOI：

  10.1021/ol034873k
• 作为产物：
  描述：

  4-hydroxy-6-methyl-3-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2-pyrone 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以100%的产率得到4-hydroxy-6-methyl-3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2-pyrone
  参考文献：
  名称：

  Synthetic Studies Directed toward the Assembly of the C-Glycoside Fragment of the Telomerase Inhibitor D8646-2-6

  摘要：

  GraphicsConstruction and characterization of the C-glycosidic moiety of telomerase inhibitor D8646-2-6 (1) are described. This is the first example of the C-glycosylation using electron-poor aromatics, 4-hydroxypyrone, as a glycosyl acceptor. The glycosylation reaction and base-promoted isomerization affords desired beta-C-glycoside in a 61% overall yield.

  DOI：

  10.1021/ol034873k

文献信息

• Polyunsaturated C-Glycosidic 4-Hydroxy-2-pyrone Derivatives: Total Synthesis Shows that Putative Orevactaene Is Likely Identical with Epipyrone A
  作者：Johannes Preindl、Saskia Schulthoff、Conny Wirtz、Julia Lingnau、Alois Fürstner

  DOI：10.1002/anie.201702189

  日期：2017.6.19

  Orevactaene and epipyrone A were previously thought to comprise the same polyunsaturated tail but notably different C‐glycosylated 4‐hydroxy‐2‐pyrone head groups. Total synthesis now shows that the signature bicyclic framework assigned to orevactaene is a chimera; the compound is almost certainly identical with epipyrone A, whose previously unknown stereochemistry has also been established during this

  以前认为Orevactaene和Epipyrone A包含相同的多不饱和尾巴，但C-糖基化的4-羟基-2-吡喃酮头基团则明显不同。现在，全合成表明，分配给orevactaene的标志性双环骨架是嵌合体。该化合物几乎可以肯定与Epipyrone A相同，而Epipyrone A在本研究中也已建立了以前未知的立体化学。成功的关键是通过使用钨和金催化的两个炔烃环异构化反应的序列，可以容易地形成推定的前内酯的双环核。同样重要的是，通过使用异双金属多不饱和模块获得的组装过程中的灵活性，其末端可以按照实际的一锅交叉耦合顺序进行选择性和连续处理。