[(2R,3R,4R,6R)-3-benzoyloxy-6-(2-hydroxynaphthalen-1-yl)-2-methyloxan-4-yl] benzoate | 128461-95-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [(2R,3R,4R,6R)-3-benzoyloxy-6-(2-hydroxynaphthalen-1-yl)-2-methyloxan-4-yl] benzoate
• CAS: 128461-95-0
• 化学式: C₃₀H₂₆O₆
• 分子量: 482.533
• InChiKey: DLFPACCADFYLRU-DRTUCXJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.85
• 重原子数：
  36.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  82.06
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  methyl 3,4-di-O-benzoyl-2,6-dideoxy-α-D-arabino-hexopyranoside 在 盐酸 、 Cp₂HfCl₂*AgClO₄ 、 4 A molecular sieve 、 氟化氢吡啶 、 溶剂黄146 作用下， 以 吡啶 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 [(2R,3R,4R,6R)-3-benzoyloxy-6-(2-hydroxynaphthalen-1-yl)-2-methyloxan-4-yl] benzoate
  参考文献：
  名称：

  Synthetic study toward vineomycins. Synthesis of c-aryl glycoside sector via Cp2HfCl2AgClO4-promoted tactics

  摘要：

  DOI：

  10.1016/s0040-4039(01)93337-4

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。
• 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.
• Convergent total synthesis of vineomycinone B2 methyl ester and its C(12)-epimer
  作者：Takashi Matsumoto、Miyoko Katsuki、Hideki Jona、Keisuke Suzuki

  DOI：10.1021/ja00018a041

  日期：1991.8

  Total syntheses of vineomycinone B2 methyl ester (7) and its C(12)-epimer (epi-7) have been completed. The key reaction for construction of the aryl C-glycoside linkage is the O --> C-glycoside rearrangement starting from D-olivosyl fluoride derivative 11 and anthrol derivative 21, which provides the regio- and stereocontrolled formation of the aryl C-glycoside sector of the target. The combination of Cp2HfCl2-AgClO4 serves as a particularly efficient promoter for this reaction. An extensive model study for attaching the side chain is presented. The Lochmann-Schlosser base cleanly effects ortho metalation of anthracene derivatives 19 and 20. The metalated species can be trapped as stannyl derivatives, from which the corresponding aryllithium species are generated by using n-BuLi or preferably MeLi in toluene. These specific reaction conditions are necessary to suppress the abnormal reaction of RLi reagents at the C(9)/C(10)-positions of the anthracenes. Coupling of the side chain moiety was efficiently carried out by such metalation of anthracene derivative 25 followed by reaction with chiral aldehyde (S)-29. The chiral aldehyde was derived from enantiomerically pure acid (S)-37 obtained by enzymatic kinetic resolution. Deoxygenation of the benzylic alcohol function followed by several steps allowed the total ynthesis of 7. Starting from (R)-aldehyde 29, the same sequence of reactions accomplished the total synthesis of epi-7. The epi series of intermediates provided firm evidence for the stereochemical homogeneity of synthetic 7.