154698-92-7

Upstream product

• 96-35-5 glycolic acid methyl ester 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 215807-85-5 1-(tert-Butyl-diphenyl-silanyloxy)-3-((R)-toluene-4-sulfinyl)-propan-2-one 
• 1278444-56-6 (R)-1-(tert-butyldiphenylsilyloxy)pent-3-yn-2-ol 
• 193292-65-8 1-(tert-butyldiphenylsilyloxy)pent-3-yne-2-one 
• 154698-93-8 2-((tertbutyldiphenylsilyl)oxy)-N-methoxy-N-methylacetamide 
• 1447756-64-0 4-((tert-butyldiphenylsilyl)oxy)-3-oxobutanenitrile 
• 93853-60-2 <(tert-butyldiphenylsilyl)oxy>acetyl chloride 
• 1400585-43-4 (S)-N-(2-tert-butyldiphenylsilyloxyacetyl)-4-isopropyl-1,3-thiazolidine-2-thione 
• 441784-82-3 1-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopropan-1-ol 

Relevant academic research and scientific papers

Sulfur-assisted domino access to bicyclic dihydrofurans: Case study and early synthetic applications

A DDQ-mediated domino reaction (up to six steps in a single process) has been developed to selectively provide substituted dihydrofurans from a common starting material containing a cyclic bis-thioenol ether. Study of the reaction mechanism highlighted a role played by the sulfur-containing moiety in influencing reaction rate and stereoselectivity.

COMPOUNDS AND METHODS FOR THE TREATMENT OF OCULAR DISORDERS

Described herein are compositions and methods for the treatment of ocular surface disorders including meibomian gland dysfunction, blepharitis, dry eye disease and other inflammatory/ infections disease of the anterior surface of the eye. Said compositions and methods comprise keratolytic conjugate which demonstrate keratolytic activity, and anti-inflammatory or other desirable activities. Topical administration of said compositions to the eye, ocular surface or surrounding areas provides therapeutic benefit to patients suffering from ocular surface disorders.

Direct anti Glycolate Aldol Reaction of Protected Chiral N-Hydroxyacetyl Thiazolidinethiones with Acetals Catalyzed by a Nickel(II) Complex

The direct and stereocontrolled addition of (S)-4-isopropyl-N-(2-pivaloyloxyacetyl)-1,3-thiazolidine-2-thione to dialkyl acetals of aromatic and α,β-unsaturated aldehydes catalyzed by 2.5–5 mol-% of a nickel(II) complex permits the synthesis of diastereom

Pyrazolotriazines as inhibitors of nucleases

The invention provides compounds represented by the structural formula (1): wherein R1, R2, R3 and R4 are as defined in the claims. The compounds are inhibitors of nucleases, and are useful in particular in a method of treatment and/or prevention of proliferative diseases, neurodegenerative diseases, and other genomic instability associated diseases.

An efficient synthesis of the precursor of AI-2, the signalling molecule for inter-species quorum sensing

Autoinducer-2 (AI-2) is a signalling molecule for bacterial inter-species communication. A synthesis of (S)-4,5-dihydroxypentane-2,3-dione (DPD), the precursor of AI-2, is described starting from methyl glycolate. The key step was an asymmetric reduction of a ketone with (S)-Alpine borane. This new method was highly reproducible affording DPD for biological tests without contaminants. The biological activity was tested with the previously available assays and compared with a new method using an Escherichia coli reporter strain thus avoiding the use of the pathogenic Salmonella reporter.

New insights into poly(lactic- co -glycolic acid) microstructure: Using repeating sequence copolymers to decipher complex NMR and thermal behavior

Sequence, which Nature uses to spectacular advantage, has not been fully exploited in synthetic copolymers. To investigate the effect of sequence and stereosequence on the physical properties of copolymers, a family of complex isotactic, syndiotactic, and atactic repeating sequence poly(lactic-co-glycolic acid) copolymers (RSC PLGAs) were prepared and their NMR and thermal behavior was studied. The unique suitability of polymers prepared from the bioassimilable lactic and glycolic acid monomers for biomedical applications makes them ideal candidates for this type of sequence engineering. Polymers with repeating units of LG, GLG and LLG (L = lactic, G = glycolic) with controlled and varied tacticities were synthesized by assembly of sequence-specific, stereopure dimeric, trimeric, and hexameric segmer units. Specifically labeled deuterated lactic and glycolic acid segmers were likewise prepared and polymerized. Molecular weights for the copolymers were in the range Mn = 12-40 kDa by size exclusion chromatography in THF. Although the effects of sequence-influenced solution conformation were visible in all resonances of the 1H and 13C NMR spectra, the diastereotopic methylene resonances in the 1H NMR (CDCl3) for the glycolic units of the copolymers proved most sensitive. An octad level of resolution, which corresponds to an astounding 31-atom distance between the most separated stereocenters, was observed in some mixed sequence polymers. Importantly, the level of sensitivity of a particular NMR resonance to small differences in sequence was found to depend on the sequence itself. Thermal properties were also correlated with sequence.

Highly enantiopure (tert-butyldiphenylsilyloxymethyl)oxiranes from barium carbonate

The synthesis of (2R)-(tert-butyldiphenylsilyloxymethyl)oxirane and the (2S)-enantiomer from barium carbonate was developed. Methyl glycolate or the hydroxamate analog was prepared and in turn reacted with (S)-(-)-methyl p- tolylsulfoxide or the (R)-enantiomer to make β-keto sulfoxides. From the sulfoxides, we made the diastereoisomeric alcohols in a highly selective sulfoxide group directed hydride reduction, and a Pummerer rearrangement reaction followed by deprotection yielded the enantiomeric diols. (2R)- (tert-Butyldiphenylsilyloxymethyl)oxirane and its (2S)-enantiomer were derived from these diols in an overall yield of 56 % from barium carbonate. This method was developed to provide a convenient access to isotope-labeled analogs of these compounds.

A Remarkable Substituent Effect on the Enantioselectivity of Tandem Asymmetric Epoxidation and Enantiospecific Ring Expansion of Cyclopropylidene Alcohols: A New Enantiocontrolled Synthesis of (-)-Debromoaplysin and (-)-Aplysin

A remarkable substituent effect by the tert-butyldimethylsiloxy group on the enantioselectivity of the tandem asymmetric epoxidation and enantiospecific ring expansion of 2--2-cyclopropylideneethanol (18), affording (S)-(-)-2--2-hydroxymethylcyclobutanone (21) in high yield and high enantiomeric excess, was observed.This enabled us to accomplish a concise and highly enantioselective total synthesis of (-)-debromoaplysin (2) and (-)-aplysin (1), providing a new and general strategy for the enantioselective synthesis of biologically important substances having the dihydrobenzofuran framework.