Selective Synthesis of Glyceryl Tris[9,10‐(<i>threo</i>)‐dihydroxyoctadecanoate]
Bibliographic record
Abstract
Abstract Elaborating novel triacylglyceride (TAG) based polyester hyperbranched unimolecular encapsulating agents represents an original and promising approach to the selective delivery of hydrophobic biologically active compounds. However, selective modification of double bonds in unsaturated TAG to obtain corresponding pure polyhydroxy derivatives with high yields is still a big challenge. Two novel approaches to synthesize the glyceryl tris[9,10‐( threo )‐dihydroxyoctadecanoate] were proposed and tested: (1) via the bromination and nucleophilic substitution of secondary halide functions by oxyacetyl groups followed by the hydrolysis of acetyls, and (2) direct transformation of the double bonds by the reaction with peroxoformic acid in an excess of formic acid, and the removal of formyl protective groups. Glycerol trioleate and natural olive oil were used as starting materials. The first synthetic route allowed for successful preparation of the corresponding polyhalide and polyoxyacetyl products; however, a more effective final deacetylation procedure is required. The second proposed approach showed a very good reproducibility in obtaining hydroxy‐oxyformyl derivatives. The optimal conditions of the reaction involve the use of diethyl ether as a cosolvent and stirring at room temperature for 30 min. To remove the formyl groups, three original procedures using organic solvent medium at room temperature were proposed: in the presence of cesium carbonate in chloroform–methanol mixture, and two methods using hydrochloric acid in chloroform–methanol mixture or in acetone. All three methods were efficient to carry out the deformylation; nevertheless, TAG esters remained stable only with 15–17 % hydrochloric acid in acetone. Simple isolation procedures and high overall yields (95.6 and 94.9 % for both triolein and olive oil, respectively) allow considering the second approach as a promising method to obtain threo ‐polyhydroxy derivatives from unsaturated TAG.
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How this classification was reachedexpand
Full frame distilled prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.000 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.001 | 0.001 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.001 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.001 | 0.000 |
Machine scores (provisional)
The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.
Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from itClassification
machine, unvalidatedMachine predicted; a candidate call from one teacher head, not a consensus.
How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".