56586-08-4

Upstream product

• 56552-80-8 (R)-3-benzyloxy-1,2-propanediol 
• 112-76-5 Stearoyl chloride 
• 111-63-7 vinyl stearate 
• 4145-51-1 3-O-Benzyl-1-O-octadecanoyl-sn-glycerin 
• 57-11-4 stearic acid 
• 638-08-4 stearic anhydride 
• 16495-03-7 (S)-4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 

Downstream Products

• 195970-40-2 Octadecanoic acid (R)-2-(benzyloxy-diisopropylamino-phosphanyloxy)-1-octadecanoyloxymethyl-ethyl ester 
• 1429-59-0 1,2-distearoyl-sn-glycerol 

Relevant academic research and scientific papers

Synthesis and enantiospecific analysis of enantiostructured triacylglycerols containing n-3 polyunsaturated fatty acids

The stereospecific structure of triacylglycerols (TAGs) affects the bioavailability of fatty acids. Lack of enantiopure reference compounds and effective enantiospecific methods have hindered the stereospecific analysis of individual TAGs. Twelve novel enantiostructured AAB-type TAGs were synthesized containing one of the three n-3 polyunsaturated fatty acid: α-linolenic acid (ALA), eicosapentaenoic acid (EPA), or docosahexaenoic acid (DHA) in sn-1 or sn-3 position. These compounds formed six enantiomer pairs, which were separated with recycling high-performance liquid chromatography using chiral columns and UV detection. The chromatographic retention behavior of the enantiomers and the stereospecific elution order were studied. The enantiomer with an n-3 PUFA in the sn-1 position eluted faster than the enantiomer with the n-3 PUFA in the sn-3 position, regardless of the carbon chain length and number of double bonds of the PUFA. TAG enantiomers containing DHA exhibited highly different retention on the chiral column and were separated after the first column, whereas recycling was needed to separate the enantiomer pairs containing ALA or EPA. The system using two identical columns and one mobile phase, without sample derivatization, proved to be very effective also for peak purity assessment, confirming the enantiopurity of the synthesized structured TAGs being higher than 98 percent (96 percent ee).

Preparation, supramolecular aggregation and immunological activity of the bona fide vaccine adjuvant sulfavant S

In aqueous conditions, amphiphilic bioactive molecules are able to form self-assembled colloidal structures modifying their biological activity. This behavior is generally neglected in preclinical studies, despite its impact on pharmacological development. In this regard, a significative example is represented by a new class of amphiphilic marine-inspired vaccine adjuvants, collectively named Sulfavants, based on the β-sulfoquinovosyl-diacylglyceride skeleton. The family includes the lead product Sulfavant A (1) and two epimers, Sulfavant R (2) and Sulfavant S (3), differing only for the stereochemistry at C-2 of glycerol. The three compounds showed a significant difference in immunological potency, presumably correlated with change of the aggregates in water. Here, a new synthesis of diastereopure 3 was achieved, and the study of the immunomodulatory behavior of mixtures of 2/3 proved that the bizarre in vitro response to 1–3 effectively depends on the supramolecular aggregation states, likely affecting the bioavailability of agonists that can effectively interact with the cellular targets. The evidence obtained with the mixture of pure Sulfavant R (2) and Sulfavant S (3) proves, for the first time, that supramolecular organization of a mixture of active epimers in aqueous solution can bias evaluation of their biological and pharmacological potential.

PHOSPHATIDYLINOSITOL

The invention relates to a new pharmaceutical compound, diacyl phosphatdylinositol in which both the sn-1 and the sn-2 place are taken by stearic acid (18:0) (diacyl [18:0; 18:0] phosphatidylinositol), more preferably, wherein said diacyl phosphatidylinositol is compound 1 as depicted in Fig. 10 or a racemate of compounds 1 and 2 as depicted in Fig. 10. Said pharmaceutical compound and pharmaceutical compositions comprising this compound are specifically useful for the treatment of a disease or a condition wherein suppression of T-cell activation is desirable, such as asthma, diabetes Type 1, rheumatoid arthritis, inflammatory bowel disease or psoriasis. Also part of the invention are food items containing the compound(s) of the invention and use thereof in a diet to treat or prevent the disease or condition mentioned above

Structural determination of sulfoquinovosyldiacylglycerol by chiral syntheses

Chiral sulfoquinovosyldiacylglycerols (SQDGs) have been synthesized to determine the absolute stereochemistry and the biological activities. The 1 H NMR spectrum of a natural SQDG is comparable to that of synthetic (2S)-SQDG rather than that of the (2R) analogue. The biological activity of the respective isomers for DNA polymerase α and β inhibition was not distinguishable in the enzymatic assay.

A simple and efficient method for direct acylation of acetals with long alkyl-chain carboxylic acid anhydrides

We have developed an efficient and simple method for direct transformation of acetals to carboxylic acid esters. The method consists of treatment of acetals with carboxylic anhydrides in the presence of boron trifluoride etherate as a catalyst and affords the corresponding ester derivatives in high yields with retention of configuration in the alcohol moiety. Some mechanistic aspects of this synthetically useful transformation are also discussed. (C) 2000 Elsevier Science Ltd.

Phosphorylation of unnatural phosphatidylinositols with phosphatidylinositol 3-kinase

Phosphatidylinositol analogs (PI(C2)-PI(C18)) having a series of saturated fatty acid (C2-C18) at sn-2 position were synthesized and subjected to the phosphorylation reaction with phosphatidylinositol 3-kinase (PI 3- kinase). The reactivity of Pica with PI 3-kinase turned out to be comparable to that of natural PI, although PI(C18) was not phosphorylated under the same condition. The chirality of sn-2 center was not responsible for the phosphorylation reaction. (C) 2000 Elsevier Science Ltd.