Syntheses of Orthogonally Protected <scp>d‐</scp>Galactosamine, <scp>d</scp>‐Allosamine and <scp>d</scp>‐Gulosamine Thioglycoside Building Blocks with <i>N</i>‐phthalimido Groups
Bibliographic record
Abstract
Abstract Amino sugars, d‐galactosamine (2‐deoxy‐2‐aminogalactose), d‐allosamine (2‐deoxy‐2‐aminoallose) and d‐gulosamine (2‐deoxy‐2‐aminogulose) are components of several important carbohydrates of biologically relevant systems and in the area of therapeutics. In this work, we report the syntheses of their orthogonally protected N‐phthalimido thioglycoside derivatives from d‐glucosamine as building blocks for potential applications in further syntheses of their complex carbohydrates. The syntheses rely on installing orthogonal protections on N‐pthalimido glucosamine thioglycoside followed by Lattrell‐Dax inversions at C4 or C3, via the triflates, to yield d‐galactosamine or d‐allosamine, each of which is then readily converted to the d‐gulosamine derivative by inversions at either C3 of the former or C4 of the latter. The utility of the synthesized building blocks is also demonstrated by the stereoselective and exclusive synthesis of the β‐disaccharide in a proof of concept glycosylation reaction.
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How this classification was reachedexpand
Full frame machine prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.
Distilled classifier scores by category (both heads)
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.000 |
| Meta-epidemiology (narrow) | 0.001 | 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) | 0.001 | 0.001 |
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 source (direct Gemma or distilled Codex), 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".