Efficient Synthesis of <i>p‐Tolyl</i> 6‐Deoxy‐ <scp>d</scp> ‐Heptopyranose Thioglycosides
Bibliographic record
Abstract
Capsular polysaccharides from a range of bacteria, notably campylobacters, possess 6‐deoxy‐heptose residues. Synthetic fragments of these polysaccharides have myriad applications in both fundamental and applied research, but few efficient routes for accessing these monosaccharides in a form suitable for glycosylation reactions are available. The synthesis of thioglycosides of 6‐deoxy‐ d ‐ manno ‐, 6‐deoxy‐ d ‐ talo ‐, and 6‐deoxy‐ d ‐ altro ‐heptoses from a single commercially available and inexpensive monosaccharide, methyl α‐ d ‐mannopyranoside, is reported here. The route involves C‐6 homologation and, in some cases, configurational inversion at C‐3 or C‐4. These routes provide access to glycosyl donors of three of the four naturally occurring 6‐deoxy‐ d ‐heptopyranoses, complementing previous work that has provided glycosyl donors of fourth such monosaccharide, 6‐deoxy‐ d ‐ ido ‐heptopyranose.
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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) | 0.000 | 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 | 0.001 |
| Insufficient payload (model declined to judge) | 0.002 | 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".