Facile route for the synthesis of the iminosugar nucleoside (3R,4R)-1-(pyren-1-yl)-4-(hydroxymethyl)pyrrolidin-3-ol.
N-(Pyren-1-yl)-(3R,4S)-4-[(1S,2R)-1,2,3-trihydroxypropyl]pyrrolidin-3-ol (4) was obtained in 36% yield from 3-deoxy-3-C-formyl-1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose (3) by combined hydrolysis and aminoalkylation reactions with 1-aminopyrene in a one-pot reaction. Cleavage reactions of the exocyclic triol chain in 4 with NaIO4 and NaBH4 resulted in iminosugars 7 and 8, which are analogues of the furanose forms of 2-deoxy-D-allose and of 2-deoxy-d-ribose, the latter analogue N-(pyren-1-yl)-(3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol (8) being formed in 83% yield.
Hassan
Allam A
AA
Nucleic Acid Center, Department of Chemistry, University of Southern Denmark, Odense University, DK-5230 Odense M, Denmark.
Jørgensen
Per T
PT
Stein
Paul C
PC
Fattah
M E Abdel
ME
el-Gawad
Ibrahim I A
II
Pedersen
Erik B
EB
D000478:Alkylation; D000586:Amination; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D011721:Pyrenes / Q000138:chemical synthesis* / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry
C494580:1-(pyren-1-yl)-4-(hydroxymethyl)pyrrolidin-3-ol; D009705:Nucleosides; D011721:Pyrenes; D011759:Pyrrolidines