Allyl protecting group mediated intramolecular aglycon delivery (IAD): Synthesis of α-glucofuranosides and β-rhamnopyranosides

Tetrahedron

Volumn 60, Issue 41, 2004, Pages 9061-9074

  Cumpstey, Ian ^a   Fairbanks, Antony J ^a   Redgrave, Alison J ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Carbohydrates; Glycosylation; Intramolecular aglycon delivery (IAD); Stereocontrol; Thioglycosides

Indexed keywords

GLUCOSE; GLUCOSE DERIVATIVE; GLUCOSIDE; PYRAN DERIVATIVE;

ALLYLATION; ARTICLE; CIS ISOMER; CROSS LINKING; GLYCOSYLATION; MOLECULAR INTERACTION; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM; STEREOSPECIFICITY; SYNTHESIS; TRANS ISOMER;

EID: 4444257484     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.07.083     Document Type: Article

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38. Studies were in fact also carried out on the minor α-anomer 19α, which was carried through an analogous reaction sequence to that undertaken for 19β (Scheme 4). However, all subsequent IAD experiments on tethered materials derived from the α-donor, in which the leaving group is syn to the 2-hydroxyl group, revealed that whilst intramolecular glycosylation did occur that this was substantially less efficient than for the epimeric donor, in which the anomeric leaving group is anti to the 2-hydroxyl.
39. H1,H2 coupling constant, which was between 4.3 and 4.5 Hz in all cases. See Ref. 19.
40. 1H NMR spectroscopy, this material could not be efficiently separated from the also-formed manno aglycon alcohol. In addition the overall reaction yield was low (<31%), and many other unidentified products were also observed.