24583-16-2

Upstream product

• 97-30-3 methyl-alpha-D-glucopyranoside 
• 112-67-4 n-hexadecanoyl chloride 
• 14464-31-4 palmitic acid N-succinimide ester 
• 26227-65-6 palmitic acid carboimidazolide 
• 74058-64-3 1-(2-Thioxo-thiazolidin-3-yl)-hexadecan-1-one 
• 814-49-3 diethyl chlorophosphate 
• 57-10-3 1-hexadecylcarboxylic acid 
• 112-39-0 hexadecanoic acid methyl ester 
• 135363-33-6 3-palmitoyl-5-methyl-1,3,4-thiadiazole-2(3H)-thione 

Relevant academic research and scientific papers

Surfactant synthesis via lipase esterification of methyl α-d-glucopyranoside with selected aliphatic carboxylic acids

Lipase-catalyzed esterification and properties of synthesized carbohydrate esters were investigated. Methyl α-d-glucopyranoside was the acyl group acceptor and different carbon atom chain lengths of aliphatic carboxylic acids (C12, C14 and C16) as the acyl group donors were applied in the esterification. Physico-chemical studies on the synthesized carbohydrate esters were carried out. It was found that melting point for the methyl 6-O-hexadecanoyl-α-d- glucopyranoside was the highest consecutively followed by methyl 6-O-tetradecanoyl-α-d-glucopyranoside and methyl 6-O-dodecanoyl-α-d- glucopyranoside. Liquid crystal properties of the synthesized carbohydrate ester synthesized were evaluated via optical polarized microscopy. It was found that the liquid crystal textures for mono-substituted carbohydrate esters were of the smectic phase. In a quaternary system (carbohydrate ester/n-butanol/n- hexadecane/water), a maximum 34 % of water (by mass) was contained in the monophasic region of methyl 6-O-tetradecanoyl-α-d-glucopyranoside and a maximum of 52 % water (by mass) was contained in a monophasic methyl 6-O-dodecanoyl-α-d-glucopyranoside. For methyl-6-O-dodecanoyl-α-d- glucopyranoside, its concentration at aggregation was 5.2 × 10 -4 mM, with minimum air/water surface tension of 26 mN m -1. The Gibbs energy of micellization was calculated at -50 kJ mol-1. The maximum adsorption density of methyl 6-O-dodecanoyl- α-d-glucopyranoside was determined at 4 × 10-6 mol m -2 while its minimum area per surfactant molecule at the air/water surface was 47 A2.

Carbohydrate liquid crystals: Synthesis and characterisation of the methyl-6-O-(n-acyl)-α-D-glucopyranosides

Seven members of the methyl-6-O-(n-acyl)-α-d-glucopyranosides have been synthesised and their transitional properties determined. The undecanoyl and octadecanoyl members do not exhibit liquid crystallinity while the members having chain lengths between dodecanoyl and hexadecanoyl exhibit a monotropic smectic A phase. Variable temperature infrared spectroscopy reveals that the hydrogen bonding within the system shows a marked change at the melting point but apparently no change at the smectic A-isotropic transition. This observation is interpreted in terms of Goodby's model for the smectic A phase in which the carbohydrate moieties are located at the centre of the smectic bilayer and assuming that hydrogen bonded aggregates persist into the isotropic phase. Within this framework, the unusually low values of the entropy change associated with the smectic A-isotropic transition may also be accounted for.

Regioselective synthesis of fatty acid esters of methyl α-D-glucopyranoside with dibutyltin dimethoxide method and biological test against staphylococcus aureus and salmonella agona

Fatty acid esters of methyl α-D-glucopyranoside were regioselectively synthesized using dibutyltin dimethoxide (DBDM) as stannylating agent, general factors affecting regioselectivity has been examined. Comparison work indicated that DBDM has some advantage as stannylating agent over dibutyltin oxide for regioselective acylation at the 2-position of unprotected methyl α-D-glucopyranoside. Microbiological tests show that methyl 2-lauryl-α-D-glucopyranoside is effective inhibitor against gram-negative bacterial Staphylococcus aures.

Ionic liquid-coated immobilized lipase for the synthesis of methylglucose fatty acid esters

A homologous series of biosurfactants has been synthesized by a novel sustainable biotransformation technique and compared with three other enzymatic processes. 6-O-Alkanoyl-methyl-α-D-glucopyranosides were obtained by lipase mediated esterification of methyl-α-D-glucopyranoside with capric acid C10:0, lauric acid C12:0, myristic acid C 14:0, palmitic acid C16:0, and oleic acid C 18:1. Solvent free transformations were compared with the use of ionic liquids and organic solvents. The lipase from Candida antarctica B, immobilized on macroporous acrylic acid beads (Novozyme 435), was employed either untreated or coated with small amounts of ionic liquids. This resulted in superior efficiencies (80%) with 1-butyl-4-methylpyridine hexafluorophosphate [4bmpy][PF6] and broader substrate tolerance in comparison to solvent free transformation. The results show a positive correlation with increasing polarity of the ionic liquids used as liquid film-coating, which was in opposition to the use of the same ionic liquid as solvent. The analysis of the ionic liquid film coated catalyst carriers was performed by optical and scanning electron microscopy (SEM). The Royal Society of Chemistry 2009.

Lipase-catalysed selective synthesis of sucrose mixed diesters

The selectivity of the esterification of sucrose was studied in the case of lipase-catalysed reactions with activated and non-activated acyl donors. Using the lipase Novozym 435, sucrose fatty acid diesters and mixed fatty acid methacrylic acid diesters w

A new highly regioselective reaction of unprotected sugars for chemical synthesis of methyl-6-D-acyl-D-glycopyranosides by means of chlorophosphoric acid diethyl ester[(C2H5O)2P(:O)Cl] as condensing reagent

A new methodology which allows the regioselective acylation of no protected methyl-D-glycopyranosides at the primary hydroxy group is described. Thus, a new synthetic procedure is presented to synthesize 6-acyl-methyl-glycopyranosides from unprotected glycopyranosides by means of (EtO)2P:OCl as condensing reagent.

SUGAR CHEMISTRY WITHOUT PROTECTING GROUPS-III. A FACILE CHEMICAL SYNTHESIS OF 6-O-ACYL-D-GLYCOPYRANOSES AND METHYL-6-O-ACYL-D-GLYCOPYRANOSIDES.

Regioselective acylation of non protected glycopyranosides was performed using 3-acylthiazolidine-2-thiones 1 and the novel 3-acyl-5-methyl-1,3,4-thiadiazole-2(3H)-thiones 2 as the acylating reagents, yielding 6-O-acylated derivatives in high yields.Acyla

SUGAR CHEMISTRY WITHOUT PROTECTING GROUPS: A NOVEL REGIOSELECTIVE SYNTHESIS OF 6-O-ACYL-D-GLUCOPYRANOSES AND METHYL-6-O-ACYL-α-D-GLUCOPYRANOSIDES

The primary hydroxyl groups of α-D-glucose and methyl-α-D-glucoside were selectively esterified by treating the free sugars with N-acylthiazolidine-2-thiones, thus affording respectively 6-O-acyl-D-glucopyranoses and methyl-6-O-acyl-α-D-glucopyranosides in high yields.This new reaction is compared with our previous synthesis of 1-O-acyl-β-D-glucopyranoses from β-D-glucose and interpreted in terms of anomeric effect.