322726-60-3Relevant academic research and scientific papers
Oxetane cis- and trans-β-amino-acid scaffolds from l-rhamnose by efficient SN2 reactions in oxetane rings; Pseudoenantiomeric analogues of the antibiotic oxetin
Johnson, Stephen W.,Jenkinson, Sarah F.,Angus, Donald,Jones, John H.,Fleet, George W.J.,Taillefumier, Claude
, p. 2681 - 2686 (2004)
An efficient multigram ring contraction of a 1,4-lactone 2-O-triflate derived from l-rhamnose - with retention of configuration in the ring closure - is the key step in the preparation of a series of oxetanes, which are pseudoenantiomeric analogues of the
cis- and trans-3-Azido-oxetane-2-carboxylate scaffolds: Hexamers of oxetane cis-β-amino acids
Barker, Sarah F.,Angus, Donald,Taillefumier, Claude,Probert, Michael R.,Watkin, David J.,Watterson, Mark P.,Claridge, Timothy D.W.,Hungerford, Natasha L.,Fleet, George W.J.
, p. 4247 - 4250 (2007/10/03)
Efficient synthesis of both cis- and trans-3-azido-oxetane-2-carboxylates relies upon efficient nucleophilic displacements of 3-O-triflates of oxetanes by trifluoroacetate and azide. Such structures are scaffolds for incorporation of oxetane-β-amino acids into oligomers; the synthesis of a series of protected β-hexapeptides and the X-ray crystal structure of methyl 2,4-anhydro-6-deoxy-5-O-benzyl-L-altronate are reported.
Two epimerisations in the formation of oxetanes from L-rhamnose: Towards oxetane-containing peptidomimetics
Johnson, Stephen W.,Angus, Donald,Taillefumier, Claude,Jones, John H.,Watkin, David J.,Floyd, Emma,Buchanan,Fleet, George W.J.
, p. 4113 - 4125 (2007/10/03)
The methyl group in (R)-3,5-O-benzylidene-L-rhamnono-1,4-lactone 2, prepared from L-rhamnose 1 in 41% yield without need for chromatography, is axial and provides a good example of Mills' rule that the 'O-inside' conformations are, in general, more stable than alternative 'H-inside' conformations. The lactone 2 may be converted in two steps in an overall 57% yield to the rhamnono-oxetane 3, which should be useful in generating oxetane dipeptide isosteres and oxetane β-amino acids and in determining the value of the oxetane ring in inducing secondary structure in small peptidomimetics. Methyl 2,4-anhydro-(S)-3,5-O-benzylidene-L-rhamnonate 11, in which both the phenyl and methyl groups are equatorial, is slightly more thermodynamically stable than 3, providing a rare exception to Mills' rule. X-ray crystal structures of 2 and 11 are reported. Copyright (C) 2000 Elsevier Science Ltd.
