108535-19-9

Upstream product

• 2280-44-6 D-Glucose 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 87316-22-1 (2R,3S,4R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol 
• 1269490-05-2 N,O-dimethyl-N-(6-O-tert-butyl-diphenylsilyl-β-D-glucopyranosyl)hydroxylamine 
• 492-61-5 β-D-glucose 

Downstream Products

• 108535-20-2 2-O-butyryl-6-O-(tert-butyldiphenylsilyl)glucose 
• 1269490-05-2 N,O-dimethyl-N-(6-O-tert-butyl-diphenylsilyl-β-D-glucopyranosyl)hydroxylamine 
• 1528764-16-0 5-(tertbutyldiphenylsilyloxymethyl)furfural 
• 180072-36-0 2,3,4-tri-O-acetyl-6-O-[(1,1-dimethylethyl)diphenylsilyl]-α-D-glucopyranosyl bromide 
• 224778-57-8 1,2,3,4-tetra-O-acetyl-6-O-tert-butyldiphenylsilyl-α/β-D-glucopyranose 

Relevant academic research and scientific papers

Tailoring chemoenzymatic oxidation: Via in situ peracids

Epoxidation chemistry often suffers from the challenging handling of peracids and thus requires in situ preparation. Here, we describe a two-phase enzymatic system that allows the effective generation of peracids and directly translate their activity to the epoxidation of olefins. We demonstrate the approach by application to lipid and olefin epoxidation as well as sulfide oxidation. These methods offer useful applications to synthetic modifications and scalable green processes.

Polyphosphates and Pyrophosphates of Hexopyranoses as Allosteric Effectors of Human Hemoglobin: Synthesis, Molecular Recognition, and Effect on Oxygen Release

Polyphosphorylated and perphosphorylated hexopyranose monosaccharides and disaccharides were synthesized from parent or partially protected carbohydrates as potential allosteric effectors of hemoglobin. A study toward the construction of seven- and eight-membered cyclic pyrophosphates was also performed on the sugars which had the proper orientation, protection, and number of phosphates. All final compounds were tested for their efficiency on oxygen release from human hemoglobin. Several compounds presented higher potency than myo-inositol hexakisphosphate, which is the most efficient of the known allosteric effectors of hemoglobin. Structure-activity relationships were analyzed. The affinity and efficiency depend on the number of phosphates attached to the carbohydrate skeleton and are related primarily to the number of negative charges present. Other effects operate, but play a lesser role.To bind or not to bind: The synthesis of polyphosphate and pyrophosphate derivatives of hexopyranoses provides a range of compounds that bind to hemoglobin and induce enhanced oxygen release. Analysis of the effects observed gives insight into structure-activity relationships. Potential medicinal applications involve the numerous diseases that display hypoxic conditions.

Critical Influence of 5-Hydroxymethylfurfural Aging and Decomposition on the Utility of Biomass Conversion in Organic Synthesis

Spectral studies revealed the presence of a specific arrangement of 5-hydroxymethylfurfural (5-HMF) molecules in solution as a result of a hydrogen–bonding network, and this arrangement readily facilitates the aging of 5-HMF. Deterioration of the quality of this platform chemical limits its practical applications, especially in synthesis/pharma areas. The model drug Ranitidine (Zantac) was synthesized with only 15 % yield starting from 5-HMF which was isolated and stored as an oil after a biomass conversion process. In contrast, a much higher yield of 65 % was obtained by using 5-HMF isolated in crystalline state from an optimized biomass conversion process. The molecular mechanisms responsible for 5-HMF decomposition in solution were established by NMR and ESI-MS studies. A highly selective synthesis of a 5-HMF derivative from glucose was achieved using a protecting group at O(6) position.

SMALL MOLECULE CATALYST FOR 5-HYDROXYMETHYLFURFURAL PRODUCTION FROM SACCHARIDES

The disclosure provides the use of aryl or heteroaryl boronic acid in the preparation of 5-(hydroxymethyl)fufural (HMF) from saccharides. The aryl or heteroaryl boronic bearing electron-withdrawing groups on the aryl or heteroaryl ring of the boronic acid provided good yields. The disclosure provides a method for preparing HMF from saccharides in the presence of aryl or heteroaryl boronic acid. The disclosure provides a method for converting a saccharide other than fructose in fructose via a dehydrogenation reaction catalyzed by aryl or heteroaryl boronic acid.

Efficient synthesis of β-(1,6)-linked oligosaccharides through microwave-assisted glycosylation

A microwave-assisted glycosylation method was developed for efficient synthesis of oligosaccharides. Di-functional AB monomers, 2,3,4-tri-O-acetyl- α-d-galactopyranosyl bromide (3a) and 2,3,4-tri-O-acetyl-α-d- glucopyranosyl bromide (3b) were designed and

A new method for selective deprotection of anomeric N,O -dimethylhydroxylamine promoted by TMSCl

TMSCl was shown to be an efficient reagent for selective deprotection of the anomeric position protected as N,O-dimethylhydroxylamine glycoside. This deprotection condition was proved to be compatible with a number of protecting groups, such as the TBDPS, acetyl, benzyl, benzylidene, and benzoyl groups.Copyright Taylor and Francis Group, LLC.

Use of N,O-dimethylhydroxylamine as an anomeric protecting group in carbohydrate synthesis

The N,O-dimethyloxyamine-N-glycosides are introducedas anomerically protected building blocks for carbohydrate synthesis. These N-glycosides are stable to a variety of protecting group manipulations including acylation, alkylation, silylation, and acetal formation. The alkoxyamine-N-glycosides can be cleaved selectively with N-chlorosuccinimide to give the desired hemiacetals in excellent yield. Furthermore, these Nglycosides are stable to the activation conditions required for glycosylation using thioglycoside and trichloroacetimidate glycosyl donors suggesting N,O-dialkoxyamine-N-glycosides will be useful for complex oligosaccharide synthesis.

Synthesis of methyl secolonitoside

The monoterpene diglycoside macrolide, lonitoside 1, is assumed to be biosynthesized via the intermediate acid secolonitoside 3 which has also been isolated from Lonicera nitida E. H. Wilson. We have synthesized the methyl ester of acid 3 from D-glucose,