136982-88-2

Upstream product

• 80040-79-5 3,4,6-tri-O-benzyl-D-galactal 
• 68-12-2 N,N-dimethyl-formamide 
• 21193-75-9 D-galactal 
• 4098-06-0 triacetyl-D-galactal 
• 64-18-6 formic acid 
• 1365092-15-4 (2R,3S,4S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-iodo-3,4-dihydro-2H-pyran 
• 1092103-68-8 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-C-benzyloxymethyl-D-arabino-hex-1-enitol 

Downstream Products

• 153496-00-5 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-D-lyxo-hex-1-enitol 
• 296268-52-5 (2R,3R,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-vinyl-3,4-dihydro-2H-pyran 
• 1064077-76-4 2-C-(3,4,6-tri-O-benzyl)-galactal aldoxime 
• 1454797-06-8 (2R,3R,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(trityloxymethyl)-3,4-dihydro-2H-pyran 

Relevant academic research and scientific papers

IN VIVO ASSEMBLY OF ASGPR BINDING THERAPEUTICS

Compounds are provided that assemble together in vivo to form an ASGPR-binding compound that has an asialoglycoprotein receptor (ASGPR) binding ligand bound to an extracellular protein binding ligand for the selective degradation of the target extracellular protein in vivo to treat disorders mediated by the extracellular protein.

Palladium catalysed carbonylation of 2-iodoglycals for the synthesis of C-2 carboxylic acids and aldehydes taking formic acid as a carbonyl source

Pd catalyzed carbonylative reaction of 2-iodo-glycals has been developed taking formic acid as a carbonyl source for the synthesis of 2-carboxylic acids of sugars by the hydroxycarbonylation strategy. The methodology was successfully extended to the synthesis of 2-formyl glycals by using a reductive carbonylation approach. Both ester and ether protected glycals undergo the reaction and furnished sugar acids in good yield which is otherwise not possible by literature methods. The C-2 sugar acids were successfully utilized for the construction of 2-amido glycals, 2-dipeptido-glycal by Ugi reaction and C-1 and C-2 branched glycosyl esters.

Stereoselective synthesis of natural product inspired carbohydrate fused pyrano[3,2-: C] quinolones as antiproliferative agents

Pyrano[3,2-c]quinolone structural motifs are commonly found in natural products with diverse biological activities. As part of a research programme aimed at developing the efficient synthesis of natural product-like small molecules, we designed and developed the microwave assisted, facile stereoselective synthesis of two series of carbohydrate fused pyrano[3,2-c]quinolone derivatives (n = 23) starting from 2-C-formyl galactal and 2-C-formyl glucal, reacting with various 4-hydroxyquinolones in shorter reaction times (15-20 min). The antiproliferative activity of these synthesized pyrano[3,2-c]quinolones was determined against MCF-7 (breast) and HepG2 (liver) cancer cells. The selected library members displayed low micromolar (3.53-9.68 μM) and selective antiproliferative activity. These findings on carbohydrate fused pyrano[3,2-c]quinolone derivatives are expected to provide new leads for anticancer drug discovery.

Use of XtalFluor-E as an Alternative to POCl3 in the Vilsmeier-Haack Formylation of C-2-Glycals

We report the use of XtalFluor-E ([Et2NSF2]BF4) as an alternative to POCl3 in the Vilsmeier-Haack formylation reaction of C-2-glycals. Employing a XtalFluor-E/DMF combination allowed the desired C-2-formyl glyca

TEMPO-Catalyzed Oxidation of 3- O-Benzylated/Silylated Glycals to the Corresponding Enones Using a PIFA-Water Reagent System

A simple, highly efficient and regiospecific method for the direct conversion of 3-O-benzylated as well as silylated glycals into the corresponding enones has been developed using PIFA-TEMPO and water reagent system. The reaction is scalable on a gram sca

Stereoselective synthesis of carbohydrate fused pyrano[3,2-c]pyranones as anticancer agents

Pyrano[3,2-c]pyranone is an important structural motif present in many natural products exhibiting diverse biological activities. Two series of carbohydrate fused pyrano[3,2-c]pyranone derivatives (n = 20) were efficiently synthesized starting from 2-C-formyl galactal and 2-C-formyl glucal, reacting with various 4-hydroxycoumarins in a very short reaction time (10 min) under microwave assisted conditions. The anticancer activity of these synthesized pyrano[3,2-c]pyranones was determined in detail through cellular assays against MCF-7 (breast), MDA-MB-231 (breast) and HepG2 (liver) cancer cell lines. The newly synthesized pyrano[3,2-c]pyranones were screened for their cell-viability and anti-proliferative activity against MCF-7, MDA-MB-231 and HepG2 cell lines. Compounds 12, 13 and 14 exhibited high growth inhibitory potencies selectively against MCF-7 cells with half-maximal inhibitory concentration (IC50) values of 19.9, 14.5 and 10.9 μM respectively. Compounds 12, 13, 14, 15 and 19 inhibited the growth of MDA-MB-231 cells (breast) by 43, 44, 37, 31 and 45% respectively. However, no inhibitory effect was observed for these compounds in the human liver cancer cell line (HepG2) and normal cell lines (HEK293, human embryonic kidney cells). Mechanistic studies showed that these compounds alter the cell morphology and cause G2/M arrest in MCF-7. Further studies showed that compounds 12, 13 and 14 significantly inhibited cell migration which was accompanied by altered microtubule distribution. An enhanced accumulation of these compounds in cells was observed as compared to the 4-hydroxycoumarins precursor in the intracellular uptake assay. These findings confirm that carbohydrate fused pyrano[3,2-c]pyranones are better candidates for anticancer activity.

Polyunsaturated C-Glycosidic 4-Hydroxy-2-pyrone Derivatives: Total Synthesis Shows that Putative Orevactaene Is Likely Identical with Epipyrone A

Orevactaene and epipyrone A were previously thought to comprise the same polyunsaturated tail but notably different C-glycosylated 4-hydroxy-2-pyrone head groups. Total synthesis now shows that the signature bicyclic framework assigned to orevactaene is a chimera; the compound is almost certainly identical with epipyrone A, whose previously unknown stereochemistry has also been established during this study. Key to success was the ready formation of the bicyclic core of putative orevactaene by a sequence of two alkyne cycloisomerization reactions using tungsten and gold catalysis. Equally important was the flexibility in the assembly process gained by the use of heterobimetallic polyunsaturated modules whose termini could be selectively and consecutively addressed in a practical one-pot cross-coupling sequence.

Synthesis of dihydroxymethyl dihydroxypyrrolidines and steviamine analogues from C-2 formyl glycals

Synthesis of dihydroxymethyl dihydroxypyrrolidines from C-2 formyl d-glycals has been described via a common dicarbonyl intermediate. The hence obtained pyrrolidines have been further utilized for the synthesis of some steviamine analogues. The newly synthesized molecules have been evaluated for glycosidase inhibition against 6 commercially available enzymes and found to be active in the micromolar range, where one of the steviamine analogues showed good and selective inhibition of β-mannosidase (Helix pomatia).

Synthesis of glycal-based chiral benzimidazoles by VO(acac) 2-CeCl3 combo catalyst and their self-aggregated nanostructured materials

(Figure Presented) VO(acac)2-CeCl3 combo catalyst has been developed for chemoselective cyclocondensation cum oxidation under mild reaction conditions toward synthesis of a new class of optically pure compounds, 2-(2′-C-3′,4′,6′-tri-O-benzyl/methyl-glycal)-1H- benzimidazoles. It involves an operationally simple synthetic protocol efficient for the syntheses of a wide range of chiral benzimidazoles in high yields without formation of undesired 1,2-disubstituted and pseudoglycal byproducts. Vanadium(V) is found as active oxidant for the chemical processes which is investigated by UV absorption spectroscopy. Highly ordered one-dimensional low molecular mass organic nanostructured materials are fabricated by nanocrystallization of the chiral nanoscale building blocks. Theoretical calculation by the B3LYP/6-31G** level of theory of the glycal-based chiral benzimidazoles shows out of planar geometry of the 1H-anthra[1,2-d] imidazole-6,11-dione moiety, which is responsible for the strong self-aggregation to generate ultralong nanostructured materials. We have also found nice agreement between the theoretical results with the experimental observation in 2D-NOESY experiments. The photophysical property of the solid nanostructured materials is also reported. 2009 American Chemical Society.

Generation of nitrile oxides under nanometer micelles built in neutral aqueous media: Synthesis of novel glycal-based chiral synthons and optically pure 2,8-dioxabicyclo[4.4.0]decene core

(Chemical Equation Presented) A highly efficient strategy for chemoselective oxidation of aldoximes to nitrile oxides by iodosobenzene in neutral aqueous media is reported. Their in situ intermolecular 1,3-dipolar cycloaddition (1,3-DC) with olefins in nanometer aqueous micelles occurs with improved stereoselectivity and acceleration of reaction rate toward synthesis of new chiral synthons, 3-(2′-C-3′,4′,6′-tri-O- benzylglycal)-Δ2-isoxazolines and others. Construction of optically pure 2,8-dioxabicyclo[4.4.0]decene skeleta is performed by this green approach, and the stereochemistry of the new chiral center is predicted by B3LYP density functional theory.