85618-26-4

Basic information

• Product Name: Octyl2,3,4,6-tetra-O-acetyl-b-D-thioglucopyranoside
• Synonyms: Octyl2,3,4,6-tetra-O-acetyl-b-D-thioglucopyranoside;Octyl-2,3,4,6-tetra-O-acetyl-β-D-thioglucopyranoside;Octyl 1-Thio-β-D-glucopyranoside Tetraacetate
• CAS NO: 85618-26-4
• Molecular Formula: C22H36O9S
• Molecular Weight: 476.58
• Product Categories: Carbohydrates & Derivatives
• Mol File: 85618-26-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 63-64°C
• Boiling Point: 526.1±50.0 °C(Predicted)
• Appearance: /
• Density: 1.17±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Octyl2,3,4,6-tetra-O-acetyl-b-D-thioglucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Octyl2,3,4,6-tetra-O-acetyl-b-D-thioglucopyranoside(85618-26-4)
• EPA Substance Registry System: Octyl2,3,4,6-tetra-O-acetyl-b-D-thioglucopyranoside(85618-26-4)

Safety Data

• Hazardous Substances Data: 85618-26-4(Hazardous Substances Data)

Usage

Description

Octyl2,3,4,6-tetra-O-acetyl-b-D-thioglucopyranoside is a white solid compound with the chemical name Octyl Tetra-2,3,4,6-O-acetyl-β-D-thioglucopyranoside and the CAS number 85618-26-4. It is a derivative of β-D-thioglucopyranoside, which is a modified form of glucose with a sulfur atom replacing the oxygen atom in the glycosidic linkage. Octyl2,3,4,6-tetra-O-acetyl-b-D-thioglucopyranoside is primarily used in organic synthesis.

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

• 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 
• 19879-84-6 tetraacetyl thioglucose 
• 111-66-0 oct-1-ene 
• 83-87-4 D-glucose pentaacetate 
• 111-83-1 1-bromo-octane 
• 40591-65-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiouronium bromide 

Downstream Products

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

Relevant articles and documents

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.

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.

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.