41728-14-7

Upstream product

• 4208-64-4 1-(2-furyl)ethanol 
• 1192-62-7 1-(2-furyl)-1-ethanone 
• 98-01-1 furfural 

Downstream Products

• 4394-76-7 6-methyl-2H-pyran-2-one 
• 1174754-24-5 (1R,2R,4S,6S)-2-(benzyloxy)-4-methyl-3,7-dioxabicyclo[4.1.0]-heptan-5-one 
• 1174754-25-6 (2R,3R,4S,5R,6S)-2-(benzyloxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol 
• 1174754-26-7 (2R,3R,5R,6S)-2-(benzyloxy)-6-methyltetrahydro-2H-pyran-3,5-diol 
• 71731-74-3 (2R,3S,4R,5S,6S)-2-(benzyloxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol 
• 1335126-18-5 (2R,3S,4S,5R,6S)-2-(benzyloxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol 
• 1334606-85-7 (2R,3R,6S)-2-(benzyloxy)-6-methyl-3,6-dihydro-2H-pyran-3-ol 
• 1334606-94-8 (2R,3R,6S)-2-(benzyloxy)-6-methyltetrahydro-2H-pyran-3-ol 
• 727414-86-0 (2R,6S)-2-(benzyloxy)-6-methyl-2H-pyran-3(6H)-one 
• 1334607-00-9 (2R,6S)-2-(benzyloxy)-6-methyl-3,6-dihydro-2H-pyran-3-ol 
• 1334607-07-6 (2R,6S)-2-(benzyloxy)-6-methyl-3,6-dihydro-2H-pyran-3-yl pivalate 
• 1334607-11-2 (((2R,6S)-2-(benzyloxy)-6-methyl-3,6-dihydro-2H-pyran-3-yl)oxy)(tert-butyl)dimethylsilane 
• 1334607-15-6 (2R,3S,6S)-2-(benzyloxy)-6-methyltetrahydro-2H-pyran-3-ol 
• 1334607-28-1 (2R,3S,4R,5S,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl pivalate 

Relevant academic research and scientific papers

2, 4, 5-Trideoxyhexopyranosides Derivatives of 4’-Demethylepipodophyllotoxin: De novo Synthesis and Anticancer Activity

Background: Podophyllotoxin is a natural lignan which possesses anticancer and antiviral activities. Etoposide and teniposide are semisynthetic glycoside derivatives of podophyllotoxin and are increasingly used in cancer medicine. Objective: The present work aimed to design and synthesize a series of 2, 4, 5-trideoxyhexopyrano-sides derivatives of 4’-demethylepipodophyllotoxin as novel anticancer agents. Methods: A divergent de novo synthesis of 2, 4, 5-trideoxyhexopyranosides derivatives of 4’-demethylepipodophyllotoxin has been established via palladium-catalyzed glycosylation. The abili-ties of synthesized glycosides to inhibit the growth of A549, HepG2, SH-SY5Y, KB/VCR and HeLa cancer cells were investigated by MTT assay. Flow cytometric analysis of cell cycle with propidium iodide DNA staining was employed to observe the effect of compound 5b on cancer cell cycle. Results: Twelve D and L monosaccharide derivatives 5a-5l have been efficiently synthesized in three steps from various pyranone building blocks employing de novo glycosylation strategy. D-monosaccharide 5b showed the highest cytotoxicity on five cancer cell lines with the IC50 values ranging from 0.9 to 6.7 μM. It caused HepG2 cycle arrest at G2/M phase in a concentration-dependent manner. Conclusion: The present work leads to the development of novel 2, 4, 5-trideoxyhexopyranosides derivatives of 4’-demethylepipodophyllotoxin. The biological results suggest that the replacement of the glucosyl moiety of etoposide with 2, 4, 5-trideoxyhexopyranosyl is favorable to their cytotoxic-ity. D-monosaccharide 5b was observed to cause HepG2 cycle arrest at the G2/M phase in a concen-tration-dependent manner.

Palladium-Catalyzed Regioselective and Diastereoselective C-Glycosylation by Allyl-Allyl Coupling

A Pd-catalyzed C-glycosylation reaction was developed by allyl-allyl coupling process using Achmatowicz rearrangement products as donors and methylcoumarins as acceptors under mild conditions. This method featured regio- and diastereoselectivities, stereo

Enantioselective 1,3-Dipolar [6+4] Cycloaddition of Pyrylium Ions and Fulvenes towards Cyclooctanoids

Organocatalytic enantioselective 1,3-dipolar [6+4] cycloadditions of pyrylium ion intermediates with fulvenes promoted by a chiral primary amine catalyst have been developed to proceed in moderate to good yields and high enantioselectivities. The resultant chiral bicyclo[6.3.0]undecane scaffold containing a transannular bridging ether is densely functionalised providing a rigid scaffold for further manipulations. Computational studies give important insights into the role of the primary amine catalyst. Analysis of the reaction shows that the catalytic reaction proceeds in a step-wise manner and rationalises the stereochemical outcome of the reaction. Several stereoselective complexity-generating transformations, facilitated by the diverse functional groups and transannular bridge, are presented, highlighting the versatility of the core towards a number of the cyclooctanoid natural products.

Design, Synthesis, and Phenotypic Profiling of Pyrano-Furo-Pyridone Pseudo Natural Products

Natural products (NPs) inspire the design and synthesis of novel biologically relevant chemical matter, for instance through biology-oriented synthesis (BIOS). However, BIOS is limited by the partial coverage of NP-like chemical space by the guiding NPs. The design and synthesis of “pseudo NPs” overcomes these limitations by combining NP-inspired strategies with fragment-based compound design through de novo combination of NP-derived fragments to unprecedented compound classes not accessible through biosynthesis. We describe the development and biological evaluation of pyrano-furo-pyridone (PFP) pseudo NPs, which combine pyridone- and dihydropyran NP fragments in three isomeric arrangements. Cheminformatic analysis indicates that the PFPs reside in an area of NP-like chemical space not covered by existing NPs but rather by drugs and related compounds. Phenotypic profiling in a target-agnostic “cell painting” assay revealed that PFPs induce formation of reactive oxygen species and are structurally novel inhibitors of mitochondrial complex I.

A solvent-free catalytic protocol for the Achmatowicz rearrangement

Reported here is the development of an environmentally friendly catalytic (KBr/oxone) and solvent-free protocol for the Achmatowicz rearrangement (AchR). Different from all previous methods is that the use of chromatographic alumina (Al2O3) allows AchR to proceed smoothly in the absence of any organic solvent and therefore considerably facilitates the subsequent workup and purification with minimal environmental impacts. Importantly, this protocol allows for scaling up (from milligram to gram), recycling of the Al2O3, and integrating with other reactions in a one-pot sequential manner.

Divergent Synthesis of Dihydropyranone Stereoisomers via N-Heterocyclic Carbene Catalysis

We recently developed a novel chiral N-heterocyclic carbene (NHC) catalyzed dynamic kinetic enantioselective acylation (DKEA) and dynamic kinetic diastereoselective acylation (DKDA) of Achmatowicz rearrangement products to generate useful intermediates for the further synthesis of carbohydrates. In this update, we describe a divergent NHC catalytic strategy for the stereoselective preparation of all four isomers starting from a common racemic precursor. The present report provides easy access to diverse optically pure dihydropyranones. (Figure presented.).

Lipase-Induced Oxidative Furan Rearrangements

Lipase B from Candida antarctica catalyzes the oxidative ring expansion of furfuryl alcohols using aqueous hydrogen peroxide to yield functionalized pyranones under mild conditions. The method further allows for the preparation of corresponding piperidinone derivatives by enzymatic rearrangement of N-protected furfurylamines.

Iridium-Catalyzed Dynamic Kinetic Isomerization: Expedient Synthesis of Carbohydrates from Achmatowicz Rearrangement Products

A highly stereoselective dynamic kinetic isomerization of Achmatowicz rearrangement products was discovered. This new internal redox isomerization provided ready access to key intermediates for the enantio- and diastereoselective synthesis of a series of naturally occurring sugars. The nature of the de novo synthesis also enables the preparation of both enantiomers.

Catalytic asymmetric synthesis of 8-oxabicyclooctanes by intermolecular [5+2] pyrylium cycloadditions

Highly enantioselective intermolecular [5+2] cycloadditions of pyrylium ion intermediates with electron-rich alkenes are promoted by a dual catalyst system composed of an achiral thiourea and a chiral primary aminothiourea. The observed enantioselectivity is highly dependent on the substitution pattern of the 5π component, and the basis for this effect is analyzed using experimental and computational evidence. The resultant 8-oxabicyclo[3.2.1]octane derivatives possess a scaffold common in natural products and medicinally active compounds and are also versatile chiral building blocks for further manipulations. Several stereoselective complexity-generating transformations of the 8-oxabicyclooctane products are presented. A dual thiourea catalyst system enables the title reaction to be carried out to form useful chiral building blocks that can participate in a series of complexity-generating transformations to achieve varied molecular architectures.

De novo synthesis of deoxy sugar via a Wharton rearrangement

A highly divergent synthesis of α-fuco-, α-6-deoxy-allo-, α-6-deoxy-altro-pyranosides has been achieved. This route utilizes a Wharton rearrangement as part of a new post-glycosylation transformation strategy.