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Record W2333694795 · doi:10.1021/acs.joc.5b00179

One-Pot Synthesis of Glycosyl-β-azido Ester via Diazotransfer Reaction Toward Access of Glycosyl-β-triazolyl Ester

2015· article· en· W2333694795 on OpenAlex

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

fundA Canadian funder is recorded on the work.
no affNo Canadian affiliation: this work is invisible to an affiliation-only frame.
No Canadian affiliation. An affiliation-only frame, the usual design, would never have seen this work. It is one of the works that make the case for inverting the frame.

Bibliographic record

VenueThe Journal of Organic Chemistry · 2015
Typearticle
Languageen
FieldChemistry
TopicClick Chemistry and Applications
Canadian institutionsnot available
FundersCouncil of Scientific and Industrial Research, IndiaCanadian Institute of Steel Construction
KeywordsChemistryGlycosylRegioselectivityCycloadditionAzideClick chemistryImidazoleOrganic chemistryCombinatorial chemistryCatalysis

Abstract

fetched live from OpenAlex

A concise and efficacious one-pot protocol for the synthesis of novel glycosyl-β-azido ester 3 from glycosyl olefinic ester 1 under mild conditions has been devised. The β-aminoester, formed by the conjugate addition of ammonia on olefinic ester, undergoes a metal-catalyzed diazotransfer reaction to furnish glycosyl-β-azido ester. The optimized conditions for diazotransfer reaction indicate that imidazole-1-sulphonyl azide and K2CO3 give the best results in the presence of ZnCl2. A diverse range of novel regioselective triazolyl glycoconjugates 6a-u have been achieved in high yields via 1,3-dipolar cycloaddition of compound 3 with various alkynes in the presence of CuI/DIPEA. Structures of all the compounds have been elucidated using IR, NMR, MS, and elemental analysis, and four of them (3a, 3b, 4b, and 6a) have also been characterized by single crystal X-ray diffraction analysis.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

Full frame distilled prediction

Teacher imitation

Not 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.

metaresearch head score (Codex)0.001
metaresearch head score (Gemma)0.001
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow), Insufficient payload (model declined to judge)
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.007
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.001
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0020.000

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.

Opus teacher head0.047
GPT teacher head0.278
Teacher spread0.231 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it