Acetonation of l-pentoses and 6-deoxy-l-hexoses under kinetic control using heterogeneous acid catalysts

Forsman, Jonas J.; Leino, Reko

doi:10.1016/j.carres.2010.05.002

Cited by 4 publications

(3 citation statements)

References 32 publications

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“…The residue was purified by column chromatography (60 % hexane in EtOAc) to yield (3a S ,4 S ,6 S ,6a S )‐6‐(hydroxymethyl)‐2,2‐dimethyl‐tetrahydro‐2 H ‐furo[3,4‐ d ][1,3]dioxol‐4‐ol as a yellow oil (5.3 g, 83 %). [ α ] D 21 = +22.3 ( c = 1.0, CHCl 3 ) {ref . [ α ] D 24 = +21.3 ( c = 1.02, CHCl 3 )}.…”

Section: Methodssupporting

confidence: 57%

“…13 C NMR (126 MHz, MeOD): δ = 113.2, 104.0, 88.6, 87.9, 83.4, 64.3, 26.8, 25.0 ppm. 1 H and 13 C NMR spectroscopic data match literature values . Acetic anhydride (55 mL, 580 mmol) was added to a stirred solution of (3a S ,4 S ,6 S ,6a S )‐6‐(hydroxymethyl)‐2,2‐dimethyl‐tetrahydro‐2 H ‐furo[3,4‐ d ][1,3]dioxol‐4‐ol (11 g, 58 mmol) in pyridine (200 mL) under a N 2 atmosphere at room temp.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of a Ribose‐Incorporating Medium Ring Scaffold via a Challenging Ring‐Closing Metathesis Reaction

et al. 2016

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A practical synthesis of a novel oxabicyclo[6.2.1]undecenetriol useful as a medicinal chemistry scaffold has been developed starting from l‐ribose. The sequence involves an oxidation/Grignard addition sequence and a challenging ring‐closing metathesis (RCM) reaction as the ring forming step. Exploration of the RCM substrate protecting groups revealed the key factor for successful nine‐membered medium ring formation to be conformational bias of the reacting alkenes of the RCM substrate by very bulky silyl ether protecting groups. The synthesis also allowed access to an epimeric triol and saturated and unsaturated variants of the nine‐membered ring. The medium ring conformation of the oxabicyclo[6.2.1]undecenetriol was determined by X‐ray crystallography and correlated to the solution state conformation by NMR experiments.

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Section: Methodssupporting

confidence: 57%

Section: Methodsmentioning

confidence: 99%

Synthesis of a Ribose‐Incorporating Medium Ring Scaffold via a Challenging Ring‐Closing Metathesis Reaction

et al. 2016

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“…H 2 SO 4 (0.12 mL) at rt, and the reaction mixture was stirred at rt for 3 h. The mixture was neutralized with solid NaHCO 3 , filtered, and evaporated under reduced pressure to give a colorless syrup. The residue was purified by silica gel column chromatography using hexane and ethyl acetate (1:2) as the eluent to afford 20 as a colorless syrup (4.3 g, 85%): [α] D 24 +25.3 ( c 1.05, CHCl 3 ), lit . [α] D 24 +21.3 ( c 1.02, CHCl 3 ); 1 H NMR (CD 3 OD, 400 MHz), δ 5.26 (s, 1H), 4.77 (d, J = 6.0 Hz, 1H), 4.52 (d, J = 6.0 Hz, 1H), 4.19 (irregular t, J = 4.4, 5.2 Hz, 1H), 3.63 (dd, J = 4.8, 12.0 Hz, 1H), 3.59 (dd, J = 5.6, 12.0, 1H), 1.44 (s, 3H), 1.31 (s, 3H); Anal.…”

Section: Methodsmentioning

confidence: 99%

Discovery and Structure–Activity Relationships of Novel Template, Truncated 1′-Homologated Adenosine Derivatives as Pure Dual PPARγ/δ Modulators

Kim

et al. 2020

J. Med. Chem.

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Following our report that A 3 adenosine receptor (AR) antagonist 1 exhibited a polypharmacological profile as a dual modulator of peroxisome proliferator-activated receptor (PPAR)γ/δ, we discovered a new template, 1′homologated adenosine analogues 4a−4t, as dual PPARγ/δ modulators without AR binding. Removal of binding affinity to A 3 AR was achieved by 1′homologation, and PPARγ/δ dual modulation was derived from the structural similarity between the target nucleosides and PPAR modulator drug, rosiglitazone. All the final nucleosides were devoid of AR-binding affinity and exhibited high binding affinities to PPARγ/δ but lacked PPARα binding. 2-Cl derivatives exhibited dual receptor-binding affinity to PPARγ/δ, which was absent for the corresponding 2-H derivatives. 2-Propynyl substitution prevented PPARδ-binding affinity but preserved PPARγ affinity, indicating that the C2 position defines a pharmacophore for selective PPARγ ligand designs. PPARγ/δ dual modulators functioning as both PPARγ partial agonists and PPARδ antagonists promoted adiponectin production, suggesting their therapeutic potential against hypoadiponectinemia-associated cancer and metabolic diseases.

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Protection for the Hydroxyl Group, Including 1,2‐ and 1,3‐Diols

2014

Greene's Protective Groups in Organic Synthesis

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Acetonation of l-pentoses and 6-deoxy-l-hexoses under kinetic control using heterogeneous acid catalysts

Cited by 4 publications

References 32 publications

Synthesis of a Ribose‐Incorporating Medium Ring Scaffold via a Challenging Ring‐Closing Metathesis Reaction

Synthesis of a Ribose‐Incorporating Medium Ring Scaffold via a Challenging Ring‐Closing Metathesis Reaction

Discovery and Structure–Activity Relationships of Novel Template, Truncated 1′-Homologated Adenosine Derivatives as Pure Dual PPARγ/δ Modulators

Protection for the Hydroxyl Group, Including 1,2‐ and 1,3‐Diols

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