Lanthanum-catalyzed aqueous acylation of monosaccharides by benzoyl methyl phosphate
Bibliographic record
Abstract
It was previously reported that diols dissolved in water (pH 8, EPPS buffer) react with benzoyl methyl phosphate (BMP) in the presence of lanthanide ions to form monobenzoyl esters. We have investigated the possibility of extending this process to include formation of esters of monosaccharides in water from lanthanide-catalyzed reactions with BMP. The combination of methyl-α-D-glucopyranoside and BMP in the presence of lanthanum trichloride gave selective monoacylation of the 2- and 6-hydroxyl groups in a ratio of 2:1. The likely mechanism involves preferential bisbidentate coordination of BMP and the diol to lanthanide ion (which explains how an ester forms when water is in enormous excess) followed by base-catalyzed intramolecular acyl transfer. The method should be generally applicable where a selective acylation reaction in water as solvent is desirable. Key words: benzoyl methyl phosphate, lanthanide, catalysis, water, monoacylation, selective.
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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) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.003 | 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".