Benzoic acid (2R,3S,4R,6R)-4-dimethylamino-6-(2-hydroxy-naphthalen-1-yl)-2-methyl-tetrahydro-pyran-3-yl ester | 146450-98-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Benzoic acid (2R,3S,4R,6R)-4-dimethylamino-6-(2-hydroxy-naphthalen-1-yl)-2-methyl-tetrahydro-pyran-3-yl ester
• CAS: 146450-98-8
• 化学式: C₂₅H₂₇NO₄
• 分子量: 405.494
• InChiKey: BJNULGOKSYIDHT-VVYDQYLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  59.0
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-萘酚 、 Benzoic acid (2R,3S,4R)-4-dimethylamino-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester 在 三氟甲磺酸三甲基硅酯 、 silver perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以99%的产率得到Benzoic acid (2R,3S,4R,6R)-4-dimethylamino-6-(2-hydroxy-naphthalen-1-yl)-2-methyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Aryl and Allyl C-Glycosidation Methods Using Unprotected Sugars

  摘要：

  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.

  DOI：

  10.1021/jo972146v

文献信息

• Relative Reactivities of Aminoglycosides and their Synthetic Equivalents in the C-Glycosylation of Aromatics. Synthesis of the Pseudoaglycone (d-C-Glycoside) of the Benzanthrins
  作者：Kathlyn A. Parker、Qing-jie Ding

  DOI：10.1016/s0040-4020(00)00868-1

  日期：2000.12

  benzanthrin antibiotics was prepared by a short sequence in which C-glycosylation of dehydrorabelomycin dimethyl ether served as the key step. The use of a 3-azido 2,3,6-trideoxy pyranose as an activated equivalent of a 3-dimethylamino 2,3,6-trideoxy sugar was demonstrated in this reaction.

  苯并青霉素类抗生素的伪糖苷配基是通过短序列制备的，其中脱氢雷贝霉素二甲醚的C-糖基化是关键步骤。在该反应中证明了使用3-叠氮基2,3,6-三苯氧基吡喃葡萄糖作为3-二甲基氨基2,3,6-三苯氧基糖的活化等同物。
• 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。
• Efficient C-arylglycosylation of 1-O-methyl sugar by novel use of TMSOTf-AgClO4 catalyst system
  作者：Kazunobu Toshima、Goh Matsuo、Kuniaki Tatsuta

  DOI：10.1016/0040-4039(92)88170-a

  日期：1992.4

  Highly beta-stereoselective C-arylglycosylations of the 1-O-methyl sugars 1 approximately 4 with 2-naphthol (9) were effectively achieved by novel combinational use of a catalytic amount of TMSOTf-AgClO4 as an activator. Also, C-arylglycosylations of the 1-O-acetyl sugars 5 approximately 8 with 9 in this way worked as well.