Efficient Synthesis of Azido Sugars using Fluorosulfuryl Azide Diazotransfer Reagent
Bibliographic record
Abstract
Azide-containing sugars are important tools for the synthesis of biologically relevant 1,2-cis-glycosides and for bioconjugation chemistry. Previous strategies for the installation of a non-participating C2-azido functionality use harsh conditions and long reaction times. Herein, we report the synthesis of azido sugars using fluorosulfuryl azide (FSO2N3; 1) with a Cu(II) catalyst as a safe and efficient diazotransfer reagent. Common hexosamine substrates were converted to 2-azido-2-deoxy sugars in less than 5 minutes in quantitative yield. Glycosyl donors with orthogonal protecting groups were readily prepared from these azido sugars with good overall yield and a single column purification. The diazotransfer protocol was also efficiently used on other amino sugar derivatives, including aminoglycosides and substrates with amine-containing linkers. This optimized method will expand access to important non-participating C2-azido protecting groups and other azido sugar derivatives.
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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 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.001 |
| Research integrity | 0.001 | 0.001 |
| Insufficient payload (model declined to judge) | 0.006 | 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".