N.m.r. studies of d-ribosylamines in solution: Derivatives of hydroxylamine, hydrazine, thiosemicarbazide, and secondary amines

✍ Scribed by Claude Chavis; Chantal De Gourcy; Jean-Louis Imbach

• Publisher: Elsevier Science
• Year: 1984
• Tongue: English
• Weight: 790 KB
• Volume: 135
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(84)85002-8

✦ Synopsis

N.m.r. spectroscopic studies (iH, 13C) have shown that hydroxylamine and hydrazine react with 2,3-O-isopropylidene-D-ribofuranose

(1) and D-ribose (2) to give primarily the acyclic oxime and hydrazone, respectively, whereas thiosemicarbazide affords mainly the cyclic pyranosyl and furanosyl derivatives. Acyclic or cyclic secondary amines, when condensed with either 1 or 2, furnished only mixtures of the /3-pyranosyl and P-furansyl forms, and, in some reactions, Amadori rearrangement products (2-30%).

RESULTS AND DISCUSSION

Hydroxylamine

(3), hydrazine (4)) methylhydrazine ( 5)) thiosemicarbazide ( 6), and 4-phenylthiosemicarbazide

7. were reacted severally with 2,3-O-iso-*Part II. For Part I, see ref. 1.