85618-26-4

Usage

Uses

Used in Organic Synthesis:
Octyl2,3,4,6-tetra-O-acetyl-b-D-thioglucopyranoside is used as a synthetic intermediate for the preparation of various organic compounds. Its unique structure and functional groups make it a valuable building block in the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Octyl2,3,4,6-tetra-O-acetyl-b-D-thioglucopyranoside is used as a key intermediate in the synthesis of novel drug candidates. Its ability to form stable glycosidic linkages with other molecules allows for the development of new drugs with improved pharmacological properties, such as enhanced solubility, stability, and bioavailability.
Used in Agrochemical Industry:
Octyl2,3,4,6-tetra-O-acetyl-b-D-thioglucopyranoside is also utilized in the agrochemical industry for the synthesis of new pesticides and herbicides. Its unique chemical properties enable the development of more effective and environmentally friendly agrochemicals with reduced toxicity and increased selectivity.
Used in Specialty Chemicals:
In the specialty chemicals sector, Octyl2,3,4,6-tetra-O-acetyl-b-D-thioglucopyranoside is employed as a versatile intermediate for the synthesis of various specialty chemicals, such as fragrances, dyes, and other functional materials. Its ability to form stable derivatives with a wide range of other compounds makes it an attractive building block for the development of innovative products with unique properties and applications.

Upstream product

• 19879-84-6 tetraacetyl thioglucose 
• 111-66-0 oct-1-ene 
• 111-88-6 Octanethiol 
• 604-69-3 β-D-glucose pentaacetate 
• 604-68-2 α-D-glucopyranose peracetylate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 111-83-1 1-bromo-octane 
• 40591-65-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiouronium bromide 
• 83-87-4 D-glucose pentaacetate 

Downstream Products

• 85618-21-9 octyl-beta-D-thioglucopyranoside 
• 128708-94-1 1-octylthio-1-deoxy-D-glucitol 

Relevant academic research and scientific papers

Synthesis and surface properties of alkyl β?D?thioglucopyranoside

Alkyl thioglycosides are a class of nonionic sugar-based sulfur-containing surfactants and bioreagents. The surfactants 1,2?trans alkyl β?D?thioglucopyranosides with different alkyl chain length (n = 6–12) were stereoselectively prepared by the Helferich method. Their properties including HLB number, logP value, water solubility, foam property, emulsifying property, surface property and thermotropic liquid crystal property were mainly investigated. The results showed that their HLB numbers and water-solubility decreased as the related logP values increased with increasing the alkyl chain length. Alkyl β?D?thioglucosides were already insoluble in water with n ≥ 10. Both β?D?thioglucopyranosides (n = 8, 9) reduced the surface tension of the related aqueous solution to nearly 29 mN·m?1 at the critical micelle concentration (CMC), they also had excellent foaming ability and foam stability. Nonyl β?D?thioglucopyranoside had good emulsifying properties for both n?octane/water system and toluene/water system. Alkyl β?D?thioglucopyranosides (n = 6–12) were observed to have the thermotropic liquid crystal properties.

N-Octyl (Thio)glycosides as Potential Cryoprotectants: Glass Transition Behaviour, Membrane Permeability, and Ice Recrystallization Inhibition Studies

A series of eight n-octyl (thio)glycosides (1α, β-4α, β) with d-glucose or d-galactose-configured head groups and varying anomeric configuration were synthesized and evaluated for glass transition behaviour, membrane permeability, and ice recrystallization inhibition (IRI) activity. Of these, n-octyl β-d-glucopyranoside (2β) exhibited a high glass transition temperatures (Tg), both as a neat sample and 20 wt-% aqueous solution. Membrane permeability studies of this compound revealed cellular uptake to concentrations relevant to the inhibition of intracellular ice formation, thus presenting a promising lead candidate for further biophysical and cryopreservation studies. Compounds were also evaluated as ice recrystallization inhibitors; however, no detectable activity was observed for the newly tested compounds.

Preparation of S-glycoside surfactants and cysteine thioglycosides using minimally competent Lewis acid catalysis

Here we report a method for the preparation of anomerically pure β-S-glycopyranosides (1,2-trans-glycosides) from the corresponding peracetate donors. S-glycosylation was performed in CHCl3 at reflux in the presence of a catalytic amount of InBr3. Deacylation of the intermediate peracetates were achieved under Zemplén conditions. Five pyranose examples, monosaccharides D-glucose and D-galactose and disaccharides cellobiose, maltose, and lactose, were used as donors, and five thiols including an α/ω dithiol and Fmoc-L-cysteine were used as acceptors. Melting points, high res MS, [α]D and NMR data (1H and 13C, including COSY, HSQC and HMBC) are reported for compounds not previously described.

Non-amphiphilic carbohydrate liquid crystals containing an intact monosaccharide moiety

A chiral rigid moiety which forms the basis of a new class of non-amphiphilic carbohydrate liquid crystals has been developed. This moiety contains a fully intact glucopyranose ring embedded in a trans-decalin structure. The original carbohydrate is substituted so that only two hydroxyl groups are left, resulting in derivatives with reduced hydrophilicity. The substituents R and X-R′ on the 4,6-O-ylidene β-D-glucopyranoside are in the equatorial position and can be varied extensively, using straightforward synthetic procedures. Investigations as to the requirements for R and X-R′ for inducing liquid-crystalline behavior have shown that at least one of the substituents should contain a large, polarizable aromatic moiety. An aromatic Schiff base fulfils this requirement.

Ampiphilic Carbohydrate-Based Mesogens, VI: Synthesis of a Series of Alkyl 1-Thio-D-glucopyranosides and Their Regioselective Reductions to 1-Alkylthio-1-deoxy-D-glucitols

Alkyl 1-thio-α,β-D-glucopyranosides (hexyl to decyl, 1a-e) are prepared by reaction of penta-O-acetyl-β-D-glucopyranose with the respective thiols in the presence of diethylether-trifluoroborane, followed by deacetylation. 1a-e are converted into their tetra-O-diethylboryl derivatives 2a-e and reduced with ethyldiboranes(6) in the presence of the catalyst 9-methylsulfonyloxy-9-borabicyclononane (9-BBN-mesylate, MSBBN) to give the mesogenic 1-alkylthio-1-deoxy-D-glucitols 3a-e after deboronation.

SYNTHESIS AND LIQUID CRYSTALLINE PROPERTIES OF THE n-ALKYL 1-THIO-α-D-GLUCOPYRANOSIDES, A NEW HOMOLOGOUS SERIES OF CARBOHYDRATE MESOGENS

The n-alkyl 1-thio-α-D-glucopyranosides (n-propyl to n-dodecyl) were prepared by treating 1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose with an alkanethiol in the presence of boron trifluoride etherate followed by deacetylation.The n-propyl and n-butyl derivatives are not thermotropic, the n-pentyl derivative is monotropic, and the compounds with n-hexyl and longer alkyl chains are enantiotropic, the largest liquid crystalline range being from +/- 100-175 deg for the n-undecyl derivative.The transition point data are typical for smectic behavior, and X-ray data and texture observations are indicative of a smectic Ad phase.

FREE-RADICAL ADDITION OF 1-THIOSUGARS TO ALKENES A NEW GENERAL APPROACH TO THE SYNTHESIS OF 1-THIOGLYCOSIDES

Addition of peracetylated 1-thiosugars to alkenes in the presence of azobis(isobutironitrile) (AIBN) as initiator constitutes an efficient route to alkyl 1-thioglycosides as well as to 1-thioglycosides bearing a reactive group on the aglycon.

Synthesis of Alkyl-β-D-thioglucopyranosides, a Series of New Nonionic Detergents

As a part of our search for new types of detergent useful for biological applications, a series of alkyl-β-D-thioglucopyranosides was synthesized in several steps from glucose.The overall yield was about 80percent.Critical micelle concentrations of n-hexyl-, n-heptyl-, n-octyl-, and n-nonyl-β-D-thioglucopyranoside were determined.Because of their electroneutrality, high solubility in water and high critical micelle concentration, n-heptyl- and n-octyl-β-D-thioglucopyranoside seem to be potentially useful detergents for applications in biological systems.