189996-60-9

Usage

Uses

Used in Pharmaceutical Industry:
Furo[3,4-d]-1,3-dioxol-4-ol, tetrahydro-2,2-dimethyl-, (3aR,6aR)is used as a natural anxiolytic and sedative agent for its potential to alleviate anxiety, insomnia, and other related conditions. It is considered a promising alternative to synthetic drugs due to its presence in the kava plant and its traditional use in Pacific Island cultures.
Used in Nutraceutical Industry:
Furo[3,4-d]-1,3-dioxol-4-ol, tetrahydro-2,2-dimethyl-, (3aR,6aR)can be used as an ingredient in dietary supplements and functional foods for its potential calming and sleep-promoting effects. Its natural origin and traditional use may appeal to consumers seeking natural solutions for stress and sleep disorders.
Used in Cosmetic Industry:
Furo[3,4-d]-1,3-dioxol-4-ol, tetrahydro-2,2-dimethyl-, (3aR,6aR)may be used in cosmetic products for its potential soothing and calming effects on the skin. Its presence in the kava plant, known for its traditional use in Pacific Island cultures, may provide a unique selling point for skincare products targeting stress-related skin issues.

Upstream product

• 25581-41-3 D-erythronolactone acetonide 
• 50-00-0 formaldehyd 
• 141-46-8 Glycolaldehyde 
• 67-64-1 acetone 
• 58645-35-5 3,4-O-isopropylidene-D-arabinopyranose 
• 583-50-6 D-erythrose 
• 127758-25-2 (4R,5S)-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)methan-1-ol 
• 85254-46-2 2,3-(isopropylidenedioxy)-4,4-dihydroxybutanic acid lactone 
• 127666-07-3 4,5-Dideoxy-2,3-O-isopropylidene-L-erythro-pent-4-enoic acid 

Downstream Products

• 127758-25-2 (4R,5S)-(2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)methan-1-ol 
• 444911-54-0 (3aR,4R,6aR)-N-benzyl-tetrahydro-N-hydroxy-2,2-dimethylfuro[3,4-d]-1,3-dioxol-4-amine 
• 163592-86-7 (2R,3S,4R)-N-benzyl-3,4-O-isopropylidene-2-(4-methoxybenzyl)pyrrolidine 

Relevant academic research and scientific papers

β-Selective nucleoside analog synthesis from chlorofuranoses

A method to form glycosyl linkages between nitrogen-containing heterocycles and appropriately protected furanoses is described. The method is highly beta-selective, operationally simple, and utilizes readily available reagents making the process amenable to scaleup. Representative examples of coupling between chlorofuranoses and purines or pyrrolopyrimidines are described. (C) 2000 Published by Elsevier Science Ltd.

Correlation study between A3 adenosine receptor binding affinity and anti-renal interstitial fibrosis activity of truncated adenosine derivatives

Truncated 4′-thionucleosides 1–4 and 4′-oxonucleosides 5–8 as potent and selective A3AR antagonists were synthesized from d-mannose and d-erythronic acid γ-lactone, respectively. These nucleosides were evaluated for their anti-fibrotic renoprot

SUBSTITUTED NUCLEOSIDE DERIVATIVES USEFUL AS ANTICANCER AGENTS

Compounds of the general formula (I): processes for the preparation of these compounds, compositions containing these compounds, and the uses of these compounds.

Syntheses of arabinose-derived pyrrolidine catalysts and their applications in intramolecular Diels-Alder reactions

Six chiral hydroxylated pyrrolidine catalysts were synthesized from commercially available D-arabinose in seven steps. Various aromatic substituents α to the amine can be introduced readily by a Grignard reaction, which enables facile optimization of the catalyst performance. The stereoselectivities of these catalysts have been assessed by comparing with those of MacMillan's imidazolidinone in a known intramolecular Diels-Alder (IMDA) reaction of a triene. Two additional IMDA reactions of symmetrical dienals with concomitant desymmetrisation further established the potential use of these novel amine catalysts. These pyrrolidines are valuable catalysts for other synthetic transformations.

Doubly diastereoselective conjugate additions of the antipodes of lithium N-benzyl-N-(α-methylbenzyl)amide to enantiopure ε-O-protected α,β-unsaturated esters derived from d-ribose

Enantiopure ε-O-silyloxy- and ε-O-benzyloxy-α,β- unsaturated esters derived from d-ribose, each containing a cis-dioxolane unit, display excellent (≥95:5 dr) levels of diastereofacial directing ability upon conjugate addition of achiral lithium N-benzyl-N-isopropylamide. In contrast to the corresponding enantiopure ε-O-silyloxy-α,β-unsaturated ester derived from l-tartaric acid, which contains a trans-dioxolane unit, the conjugate additions of the antipodes of lithium N-benzyl-N-(α- methylbenzyl)amide to its cis-configured counterpart result in doubly diastereoselective 'matched' and 'mismatched' reaction pairings in which the inherent reagent control serves to augment or oppose, respectively, the established substrate diastereocontrol.

Synthesis of carbohydrates in mineral-guided prebiotic cycles

One present obstacle to the "RNA-first" model for the origin of life is an inability to generate reasonable "hands off" scenarios for the formation of carbohydrates under conditions where they might have survived for reasonable times once formed. Such scenarios would be especially compelling if they deliver pent(ul)oses, five-carbon sugars found in terran genetics, and exclude other carbohydrates (e.g., aldotetroses) that may also be able to function in genetic systems. Here, we provide detailed chemical analyses of carbohydrate premetabolism, showing how borate, molybdate, and calcium minerals guide the formation of tetroses (C4H8O4), heptoses (C7H14O7), and pentoses (C 5H10O5), including the ribose found in RNA, in "hands off" experiments, starting with formaldehyde and glycolaldehyde. These results show that pent(ul)oses would almost certainly have formed as stable borate complexes on the surface of an early Earth beneath a humid CO2 atmosphere suffering electrical discharge. While aldotetroses form extremely stable complexes with borate, they are not accessible by pathways plausible under the most likely early Earth scenarios. The stabilization by borate is not, however, absolute. Over longer times, material is expected to have passed from borate-bound pent(ul)oses to a branched heptulose, which is susceptible to Cannizzaro reduction to give dead end products. We show how this fate might be avoided using molybdate-catalyzed rearrangement of a branched pentose that is central to borate-moderated cycles that fix carbon from formaldehyde. Our emerging understanding of the nature of the early Earth, including the presence of hydrated rocks undergoing subduction to form felsic magmas in the early Hadean eon, may have made borate and molydate species available to prebiotic chemistry, despite the overall "reduced" state of the planet.

Stereochemistry of enacyloxins. Part 6: Synthesis of C16′-C23′ fragments of enacyloxins, a series of antibiotics from Frateuria sp. W-315

The C16′-C23′ fragments of enacyloxins, a series of antibiotics isolated from Frateuria sp. W-315, were synthesized from D-arabinose. Copyright by Walter de Gruyter Berlin Boston.

Use of the NEO strategy (Nucleophilic addition/Epoxide Opening) for the synthesis of a new C-galactoside ester analogue of KRN 7000

Our goal in the search for potentially bioactive analogues of KRN 7000 was to design an easy synthetic approach to a library of analogues using a strategy recently developed in our laboratory based on a Nucleophilic addition followed by an Epoxide Opening

Structure-activity relationships of truncated adenosine derivatives as highly potent and selective human A3 adenosine receptor antagonists

On the basis of potent and selective binding affinity of truncated 4′-thioadenosine derivatives at the human A3 adenosine receptor (AR), their bioisosteric 4′-oxo derivatives were designed and synthesized from commercially available 2,3-O-isopr

N-Substituent effects on the diethylzinc addition to benzaldehyde catalysed by bicyclic 1,4-amino alcohols

Chiral enantiopure bicyclic 1,4-amino alcohols were synthesised by a new methodology that provided a common precursor, which was easily N-functionalised with a wide variety of substituents. The final compounds were used as chiral ligands in a model study of the enantioselective addition of diethyl zinc to benzaldehyde, aimed at understanding the influence of the N-substituent on both the rate and stereoselectivity of the reaction. This set of experiments also provided interesting insight into the non-catalysed addition that occurred by employing commercially available Et2Zn solutions.