TY - JOUR
T1 - Evidence on the structure of coyolosa. Synthesis of 6,6′-ether linked hexoses
AU - Haines, Alan H.
PY - 2004/1/19
Y1 - 2004/1/19
N2 - The structure previously reported for coyolosa, a hypoglycemic substance isolated from natural sources, as a 6,6′-ether linked pseudo-disaccharide derived from allose, is incorrect since 6-O-(6-deoxy-D-allos-6-yl)-D-allose 10, synthesised by an unequivocal route, and its derived peracetate 11, both have spectral properties, which differ from those reported for coyolosa and its peracetate. A versatile synthesis has been developed for this type of compound, containing two carbohydrate moieties joined through an ether linkage at their primary centres, which involves the displacement of a primary carbohydrate triflate with a carbohydrate alkoxide, and it allows the preparation of both symmetrical and unsymmetrical representatives of this class of compound.
AB - The structure previously reported for coyolosa, a hypoglycemic substance isolated from natural sources, as a 6,6′-ether linked pseudo-disaccharide derived from allose, is incorrect since 6-O-(6-deoxy-D-allos-6-yl)-D-allose 10, synthesised by an unequivocal route, and its derived peracetate 11, both have spectral properties, which differ from those reported for coyolosa and its peracetate. A versatile synthesis has been developed for this type of compound, containing two carbohydrate moieties joined through an ether linkage at their primary centres, which involves the displacement of a primary carbohydrate triflate with a carbohydrate alkoxide, and it allows the preparation of both symmetrical and unsymmetrical representatives of this class of compound.
KW - Acrocomia mexicana
KW - Coyolosa
KW - Ether-linked sugars
KW - Hypoglycemic
UR - http://www.scopus.com/inward/record.url?scp=0346787848&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2003.11.033
DO - 10.1016/j.tetlet.2003.11.033
M3 - Article
AN - SCOPUS:0346787848
SN - 0040-4039
VL - 45
SP - 835
EP - 837
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 4
ER -