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Record W2531838349 · doi:10.1021/acs.joc.6b01845

Diastereoselective Synthesis of C2′-Fluorinated Nucleoside Analogues Using an Acyclic Approach

2016· article· en· W2531838349 on OpenAlexafffund
Starr Dostie, Michel Prévost, Philippe Mochirian, Kashif Tanveer, Nicholas O. Andrella, Ariana Rostami, Guillaume Tambutet, Yvan Guindon

Bibliographic record

VenueThe Journal of Organic Chemistry · 2016
Typearticle
Languageen
FieldPharmacology, Toxicology and Pharmaceutics
TopicFluorine in Organic Chemistry
Canadian institutionsMcGill UniversityUniversité de MontréalMontreal Clinical Research Institute
FundersTerry Fox Research InstituteFonds Québécois de la Recherche sur la Nature et les TechnologiesWestern Canada Research GridNatural Sciences and Engineering Research Council of CanadaWellcome Trust
KeywordsChemistryMoietyNucleobaseStereochemistryNucleosideAlkylSN2 reactionAlkylationFluorineCombinatorial chemistryOrganic chemistryDNACatalysis

Abstract

fetched live from OpenAlex

2-like cyclizations of acyclic thioaminal precursors. This strategy provides access to two scaffolds, d-1',2'-cis-thiofuranosides and d-1',2'-trans-furanosides, which are difficult to generate using the standard approach for nucleoside synthesis. The addition of silylated nucleobases onto model C2-fluorinated dithioacetal substrates resulted in 1,2-syn diastereoselectivity, which is consistent with the C2-F and S-alkyl moiety being in close proximity. A new series of analogues bearing a C3' all-carbon quaternary center along with a C2'-F atom have also been synthesized using this approach and are being investigated as potential antimetabolites.

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.

How this classification was reachedexpand

Full frame machine prediction

Teacher imitation

Not 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.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation status: machine_predicted_unvalidated
Candidate categoriesnone
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 score0.003
Threshold uncertainty score0.008

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0010.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0030.001

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.

Opus teacher head0.090
GPT teacher head0.376
Teacher spread0.285 · 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

Classification

machine, unvalidated

Machine predicted; a candidate call from one source (direct Gemma or distilled Codex), not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designBench or experimental
Domainnot available
GenreEmpirical

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".

Quick stats

Citations22
Published2016
Admission routes2
Has abstractyes

Explore more

Same venueThe Journal of Organic ChemistrySame topicFluorine in Organic ChemistryFrench-language works237,207