(2R,3S,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-phenyl-3,4-dihydro-2H-pyran | 1365092-25-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-phenyl-3,4-dihydro-2H-pyran
• 英文别名: (2R,3S,4R)-5-phenyl-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran
• CAS: 1365092-25-6
• 化学式: C₃₃H₃₂O₄
• 分子量: 492.615
• InChiKey: IKTBJNGNQWHSAM-WRVRXEDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-phenyl-3,4-dihydro-2H-pyran 在 Oxone 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 21.5h， 生成 ethyl 3,4,6-tri-O-benzyl-2-C-phenyl-α-D-glucopyranoside
  参考文献：
  名称：

  Phosphine-Free Suzuki–Miyaura Cross-Coupling in Aqueous Media Enables Access to 2-C-Aryl-Glycosides

  摘要：

  A general strategy for the synthesis of 2-aryl-glycals and their elaboration to 2-C-aryl-alpha-glycosides and 1,5-anhydro-2-C-ary1-2-deoxy alditols are described. The use of reliable, efficient phosphine-free Suzuki-Miyaura cross-coupling of 2-iodoglycals in aqueous media as a key step proceeds with complete regioselectivity at C-2 and enables access to 2-aryl-glycals with different configurations in excellent yields.

  DOI：

  10.1021/ol3003139
• 作为产物：
  描述：

  3,4,6-三苄氧基-D-葡萄烯糖 在 N-碘代丁二酰亚胺 、 四(三苯基膦)钯 、 potassium carbonate 、 silver nitrate 作用下， 以 乙二醇二甲醚 、 水 、 乙腈 为溶剂， 反应 4.0h， 生成 (2R,3S,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-phenyl-3,4-dihydro-2H-pyran
  参考文献：
  名称：

  通过与Arynes的π扩环反应将取代的缩醛转化为手性熔融核。

  摘要：

  将芳烃的狄尔斯-阿尔德（Diels-Alder）加成到适当取代的乙烯基/芳基二醇上，然后通过吡喃开环进行π延伸，顺畅地提供了包含立体定义的正交保护的手性侧链的间二取代稠合芳族核。该方法在芳基同源性方面很宽泛，提供苯，萘和菲衍生物。碱诱导的去质子化，然后裂解烯丙基的CO键，似乎是导致芳香性发展的关键步骤，芳香性是环π延伸过程的驱动力。本方案可用于间二取代萘醛和醛缩酶的底物的合成。

  DOI：

  10.1021/acs.orglett.8b00319

文献信息

• Transformation of Substituted Glycals to Chiral Fused Aromatic Cores via Annulative π-Extension Reactions with Arynes
  作者：Nazar Hussain、Kalyanashis Jana、Bishwajit Ganguly、Debaraj Mukherjee

  DOI：10.1021/acs.orglett.8b00319

  日期：2018.3.16

  vinyl/aryl glycals followed by π-extension via pyran ring opening smoothly furnished meta-disubstituted fused aromatic cores containing a stereodefined orthogonally protected chiral side chain. The method is broad in terms of aryl homologation, affording benzene, naphthalene, and phenanthrene derivatives. Base-induced deprotonation followed by cleavage of the allylic C-O bond appear to be the crucial steps

  将芳烃的狄尔斯-阿尔德（Diels-Alder）加成到适当取代的乙烯基/芳基二醇上，然后通过吡喃开环进行π延伸，顺畅地提供了包含立体定义的正交保护的手性侧链的间二取代稠合芳族核。该方法在芳基同源性方面很宽泛，提供苯，萘和菲衍生物。碱诱导的去质子化，然后裂解烯丙基的CO键，似乎是导致芳香性发展的关键步骤，芳香性是环π延伸过程的驱动力。本方案可用于间二取代萘醛和醛缩酶的底物的合成。
• Ni‐Catalyzed Cross‐Coupling of 2‐Iodoglycals and 2‐Iodoribals with Grignard Reagents: A Route to 2‐ <i>C</i> ‐Glycosides and 2’‐ <i>C</i> ‐Nucleosides
  作者：Peter Polák、Janine Cossy

  DOI：10.1002/chem.202104311

  日期：2022.5.11

  2-C-glycals and ribals were then transformed into 2-C-2-deoxyglycosides, 2-C-diglycosides and 2'-C-2'-deoxynucleosides. The developed method was applied to the synthesis of a 2-chloroadenine 2'-deoxyribonucleoside - a structural analogue of cladribine (Mavenclad®, Leustatin®) and clofarabine (Clolar®, Evoltra®), two compounds used in the treatment of relapsing-remitting multiple sclerosis and hairy cell

  使用镍催化的 2-iodoglycals 和 2-iodoribal 之间的交叉偶联和格氏试剂以良好的收率合成 2-C-glycals 和 2-C-ribals。然后将制备的 2-C-糖和 ribals 转化为 2-C-2-脱氧糖苷、2-C-二糖苷和 2'-C-2'-脱氧核苷。开发的方法用于合成 2-氯腺嘌呤 2'-脱氧核糖核苷 - 克拉屈滨 (Mavenclad®, Leustatin®) 和氯法拉滨 (Clolar®, Evoltra®) 的结构类似物，这两种化合物用于治疗复发缓解多发性硬化症和毛细胞白血病。
• Highly diastereoselective 1,2-dichlorination of glycals using NCS/PPh3: study of substituent and solvent effects
  作者：Altaf Hussain、Debaraj Mukherjee

  DOI：10.1016/j.tet.2013.12.088

  日期：2014.2

  Highly diastereoselective 1,2-dichlorination of glycals has been achieved at room temperature conditions in good to excellent yields using a milder, more convenient, less hazardous reagent combination NCS/ PPh3 giving only one major product out of four possible diastereomers [either alpha-gluco (2) or alpha-manno (4)] depending upon the substituents. The diastereoselectivity is maximum (100% alpha/beta-selectivity as well as cis/trans selectivity) for D-galactal and L-rhamnal derivatives. Detailed studies showed that solvent and substituent effects play a significant role in determining the product distribution. (C) 2014 Elsevier Ltd. All rights reserved.
• Phosphine-Free Suzuki–Miyaura Cross-Coupling in Aqueous Media Enables Access to 2-<i>C</i>-Aryl-Glycosides
  作者：Isidro Cobo、M. Isabel Matheu、Sergio Castillón、Omar Boutureira、Benjamin G. Davis

  DOI：10.1021/ol3003139

  日期：2012.4.6

  A general strategy for the synthesis of 2-aryl-glycals and their elaboration to 2-C-aryl-alpha-glycosides and 1,5-anhydro-2-C-ary1-2-deoxy alditols are described. The use of reliable, efficient phosphine-free Suzuki-Miyaura cross-coupling of 2-iodoglycals in aqueous media as a key step proceeds with complete regioselectivity at C-2 and enables access to 2-aryl-glycals with different configurations in excellent yields.
• 10.1055/a-2320-6209
  作者：Chen, Shuai、Han, Yang、Chen, Anrong、Zhu, Feng

  DOI：10.1055/a-2320-6209

  日期：——

  AbstractA general strategy was developed for synthesizing 2-C-glycals through a nickel-catalyzed cross-electrophile coupling reaction of 2-iodoglycals with (hetero)aryl iodides. Key to the success of this methodology is the use of an electron-deficient bipyridyl ligand. This innovative approach facilitates the efficient construction of 2-C-glycals, thereby broadening the synthetic repertoire available for glycochemistry.