β-Fragmentation of anomeric alkoxy radicals from 1,3,4,5-tetra-O- benzyl-hex-2-ulopyranoses: A simple synthesis of new aldehydo tetrose building blocks

Synlett

Volumn , Issue 1, 1999, Pages 65-66

  Adinolfi, M ^a   Barone, G ^a   Iadonisi, A ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Aldehydo; Hex 2 ulopyranoses; Suarez reaction; Tetrose; Threose

Indexed keywords

1,3,4,5 TETRA BENZYL HEX 2 ULOPYRANOSE; RADICAL; TETROSE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG ISOLATION; DRUG SYNTHESIS; DRUG TRANSFORMATION; ENANTIOMER; GEL CHROMATOGRAPHY; OXIDATION; POLYMERIZATION; REACTION ANALYSIS;

EID: 0032912559     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2532     Document Type: Article

References (19)

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15. 2 and the organic phase was washed with aq. thiosulfate and water. Evaporation of the organic phase gave a residue which was chromatographed on a silica gel column eluted with hexane/ethyl acetate (8/2) to afford pure 2 (78 mg, 70%). Representative data for 2 and 5:
16. 2OBn).
17. The yields were generally 10-15 % higher when the conversions were performed under argon rather than under air. This observation is consistent with the known capability of oxygen of interfering in these radical fragmentations.11
18. Boto, A.; Hernandez, R.; Suarez, E. J. Org. Chem. 1995, 60, 8209 and references therein.
19. For other synthetic approaches to protected aldehydo tetroses see ref. 7a-c.