TY - JOUR
T1 - A new chemical synthesis of Ascopyrone P from 1,5-anhydro-D-fructose
AU - Andreassen, Mikkel
AU - Lundt, Inge
PY - 2006/7/24
Y1 - 2006/7/24
N2 - The naturally occurring antioxidant Ascopyrone P (1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose, 1) was prepared from the rare sugar 1,5-anhydro-D-fructose (AF, 3) in three steps in an overall yield of 36%. Thus, acetylation of 3 afforded the enolone 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-en-2-ulopyranose (4), which could be isomerised to 2,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-1-ene-3-ulose (6). Deacetylation of 6 under mild conditions gave crystalline Ascopyrone P (1).
AB - The naturally occurring antioxidant Ascopyrone P (1,5-anhydro-4-deoxy-D-glycero-hex-1-en-3-ulose, 1) was prepared from the rare sugar 1,5-anhydro-D-fructose (AF, 3) in three steps in an overall yield of 36%. Thus, acetylation of 3 afforded the enolone 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-en-2-ulopyranose (4), which could be isomerised to 2,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-1-ene-3-ulose (6). Deacetylation of 6 under mild conditions gave crystalline Ascopyrone P (1).
KW - Acetylation
KW - Fructose/analogs & derivatives
U2 - 10.1016/j.carres.2006.03.037
DO - 10.1016/j.carres.2006.03.037
M3 - Journal article
C2 - 16630602
SN - 0008-6215
VL - 341
SP - 1692
EP - 1696
JO - Carbohydrate research
JF - Carbohydrate research
IS - 10
ER -