{"doi":"10.1039/d4ra07179d","title":"Syntheses of optically active monapterin, 7,8-dihydromonapterin, and 5,6,7,8-tetrahydromonapterin from <scp>l</scp> -xylose","abstract":"We describe the syntheses of monapterin, dihydromonapterin and tetrahydromonapterin in optically active forms. The syntheses involved the condensation of l-xylose with phenylhydrazine, providing a hydrazone derivative. The reaction of the resulting hydrazone with triamino-pyrimidinone followed by oxidation of the resulting pteridinone with molecular oxygen furnished pterin containing a hydroxylated side chain. Hydrogenation of the pterin derivatives over RANEY® Ni catalyst afforded dihydromonapterin and tetrahydromonapterin in optically active forms. We also investigated an alternative route involving an Amadori rearrangement, followed by the Polonovski-Boon reaction as the key step to make these monapterin derivatives.","journal":"RSC Advances","year":2024,"id":482143,"datarank":0.0,"base_score":0.0,"endowment":0.0,"self_citation_contribution":0.0,"citation_network_contribution":0.0,"self_endowment_contribution":0.0,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":1,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9524,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2024-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":951059,"name":"Ashish Sharma","orcid":"0000-0003-1428-3542","position":1,"is_corresponding":false},{"id":1322775,"name":"Satish Nagam","orcid":null,"position":2,"is_corresponding":false},{"id":454440,"name":"Clay Fuqua","orcid":"0000-0001-7051-1760","position":3,"is_corresponding":false},{"id":233704,"name":"Arun K. Ghosh","orcid":"0000-0003-2472-1841","position":0,"is_corresponding":true}],"reference_count":30,"raw_metadata":null,"created_at":"2026-07-19T02:07:14.349221Z","pmid":"39524087","pmcid":null,"fwci":null,"citation_percentile":null,"influential_citations":0,"oa_status":null,"license":null,"views":0,"total_file_size_bytes":0,"version_count":0,"fair_f":null,"fair_a":null,"fair_i":null,"fair_r":null,"fair_zscore":null,"fair_rationale":null,"fair_model":null,"fair_agent_version":null,"fair_fulltext_source":null,"fair_has_llm":null,"fair_computed_at":null,"clinical_trials":[],"software_tools":[],"db_accessions":[],"linked_datasets":[],"topics":[]}