(2R,3S,4R,6R)-6-(2-Hydroxy-naphthalen-1-yl)-2-methyl-tetrahydro-pyran-3,4-diol | 146347-23-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2R,3S,4R,6R)-6-(2-Hydroxy-naphthalen-1-yl)-2-methyl-tetrahydro-pyran-3,4-diol
• 英文别名: (2R,3S,4R,6R)-6-(2-hydroxynaphthalen-1-yl)-2-methyloxane-3,4-diol
• CAS: 146347-23-1
• 化学式: C₁₆H₁₈O₄
• 分子量: 274.317
• InChiKey: OUQRHOATUBACCZ-APGPQJPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl D-olivoside 、 2-萘酚 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以98%的产率得到(2R,3S,4R,6R)-6-(2-Hydroxy-naphthalen-1-yl)-2-methyl-tetrahydro-pyran-3,4-diol
  参考文献：
  名称：

  由未保护的甲基糖苷和1-羟基糖合成芳基C-糖苷的改良实用方法

  摘要：

  使用TMSOTf对未保护的甲基糖苷9-12和未保护的1-羟基糖14和15以及2-萘酚6进行芳基C糖基化作用比酰化的甲基糖苷4和5更为有效。未保护的甲基糖苷10还可与其他苯酚和萘酚衍生物25-27平滑偶联，从而以高收率获得相应的未保护的邻羟基芳基β- C-糖苷（TMSOTf =三甲基甲硅烷氧基三氟甲磺酸酯）。

  DOI：

  10.1039/c39940000997

文献信息

• c-Arylglycosylation of unprotected free sugar
  作者：Kazunobu Toshima、Goh Matsuo、Toru Ishizuka、Masaya Nakata、Mitsuhiro Kinoshita

  DOI：10.1039/c39920001641

  日期：——

  Highly regio- and stereo-selective C-arylglycosylations of the protected free sugars 1–4, the unprotected methyl glycosides 6–9 and the unprotected free sugars 10 and 11 with 2-naphthol 5 are effectively realized by the combined use of TMSOTf–AgClO4(TMSOTf = trimethylsilyloxytrifluoromethanesulfonate) as a catalytic activator.

  通过 TMSOTf-AgClO4 的组合使用，可以有效实现受保护的游离糖 1-4、未受保护的甲基糖苷 6-9 以及未受保护的游离糖 10 和 11 与 2-萘酚 5 的高度区域和立体选择性 C-芳基糖基化（TMSOTf = 三甲基硅氧基三氟甲磺酸盐）作为催化活化剂。
• An imrpoved practical method for synthesis of aryl C-glycosides from unprotected methyl glycosides and 1-hydroxy sugars
  作者：Kazunobu Toshima、Goh Matsuo、Masaya Nakata

  DOI：10.1039/c39940000997

  日期：——

  Aryl C-glycosidations of the unprotected methyl glycosides 9–12 and the unprotected 1-hydroxy sugars 14 and 15 with 2-naphthol 6 using TMSOTf proceed much more effectively than those of the acylated methyl glycosides 4 and 5; the unprotected methyl glycoside 10 is also smoothly coupled with other phenol and naphthol derivatives 25–27 to give the corresponding unprotected o-hydroxyaryl β-C-glycosides

  使用TMSOTf对未保护的甲基糖苷9-12和未保护的1-羟基糖14和15以及2-萘酚6进行芳基C糖基化作用比酰化的甲基糖苷4和5更为有效。未保护的甲基糖苷10还可与其他苯酚和萘酚衍生物25-27平滑偶联，从而以高收率获得相应的未保护的邻羟基芳基β- C-糖苷（TMSOTf =三甲基甲硅烷氧基三氟甲磺酸酯）。
• Aryl and Allyl <i>C</i>-Glycosidation Methods Using Unprotected Sugars
  作者：Kazunobu Toshima、Goh Matsuo、Toru Ishizuka、Yasunobu Ushiki、Masaya Nakata、Shuichi Matsumura

  DOI：10.1021/jo972146v

  日期：1998.4.1

  Practical and highly stereoselective aryl and allyl C-glycosidation methods using unprotected sugars as glycosyl donors have been developed. Aryl C-glycosidations of several unprotected 2-deoxy sugars with phenol and naphthol derivatives by the combined use of trimethylsilyl trifluoromethanesulfonate (TMSOTf)-AgClO4 or TMSOTf exclusively gave the corresponding unprotected o-hydroxyaryl beta-C-glycosides which appear in many biologically attractive aryl C-glycoside antibiotics as the key subunit. On the other hand, allyl C-glycosidations of several unprotected glycals with allyltrimethylsilane by TMSOTf afforded the corresponding unprotected and 2,3-unsaturated allyl alpha-C-glycosides in high yields which are versatile synthetic intermediates for the syntheses of optically active natural products.
• Aryl C-glycosylation using an ionic liquid containing a protic acid
  作者：Chigusa Yamada、Kaname Sasaki、Shuichi Matsumura、Kazunobu Toshima

  DOI：10.1016/j.tetlet.2007.04.077

  日期：2007.6

  Aryl C-glycosylation of several glycosyl donors, including unprotected sugars, with phenol and naphthol derivatives in an ionic liquid containing a protic acid proceeded effectively and stereoselectively to give the corresponding aryl C-glycosides in good to high yields. Because the ionic liquid was nonvolatile, the reaction could be carried out under reduced pressure; in addition, the ionic liquid could be reused without loss of effectiveness. These features contribute to the significant advantages of this novel aryl C-glycosylation reaction. (c) 2007 Elsevier Ltd. All rights reserved.