Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1988-05-05
1990-06-19
Brown, Johnnie R.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 187, 536122, 536124, 562433, C07H 1102
Patent
active
049355031
ABSTRACT:
The invention describes a one-pot single step procedure for the azidochlorination or diazidization of glycals, including glycal elements of carbohydrates. Compounds such as 3,4,6-tri-O-benzyl-2-azido-2-deoxy-alpha-D-galactopyranosy chloride, and 3,4,6-tri-O-benzyl-2-azido-2-deoxy-alpha-,beta-D-galactopyranose are prepared from tri-O-benzyl galactal as well as 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-alpha-galactopyranasol chloride and 3,6-di-O-acetyl-4-O-[2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl]-2-azi do-2-deoxy-alpha-D-glycopyranosyl chloride from their respective O-acetylated glycal derivatives by the addition of azido chloride which is chemically generated in situ. A method using 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl chloride for the synthesis of antigenic determinants such as the terminal asialo GM.sub.1 (beta-D-Gal (1->3)-beta-D-GalNAc-OR) has been demonstrated. The conversion of the subject synthon into 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide and 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranose is also described. A further method for the synthetic generation of the Tn antigen (alpha-D-GalNAc-O-L-serine) is also described.
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Naicker Selvaraj
Noujaim Anthony A.
Biomira, Inc.
Brown Johnnie R.
Cooper Iver P.
Peselev Elli
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