TY - JOUR
T1 - Synthesis of the Disaccharide Moiety of Bleomycin. 2-O-(3-O-Carbamoyl-α-D-mannopyranosyl)-L-gulopyranose Derivatives
AU - Katano, Kiyoaki
AU - Millar, Alan
AU - Pozsgay, Vince
AU - Primeau, John L.
AU - Hecht, Sidney M.
PY - 1986
Y1 - 1986
N2 - The synthesis of the carbohydrate moiety of bleomycin [2-O-(3-O-carbamoyl-α-D-mannopyranosyl)-L-gulo-pyranose] is described. A key parameter in defining a successful strategy was the lability of the carbamoyl group. Several approaches were investigated; the most successful involved the coupling of 1,6-di-O-acetyl-3,4-di-O-benzyl-β-L-gulopyranose (19) and 2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl chloride (17) via the agency of silver trifluoromethanesulfonate and tetramethylurea. Also reported is the synthesis of l,6-di-O-acetyl-3,4-di-O-benzyl-2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-gulopyranose (16), a dissacharide useful for the synthetic elaboration of decarbamoyl bleomycin.
AB - The synthesis of the carbohydrate moiety of bleomycin [2-O-(3-O-carbamoyl-α-D-mannopyranosyl)-L-gulo-pyranose] is described. A key parameter in defining a successful strategy was the lability of the carbamoyl group. Several approaches were investigated; the most successful involved the coupling of 1,6-di-O-acetyl-3,4-di-O-benzyl-β-L-gulopyranose (19) and 2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl chloride (17) via the agency of silver trifluoromethanesulfonate and tetramethylurea. Also reported is the synthesis of l,6-di-O-acetyl-3,4-di-O-benzyl-2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-gulopyranose (16), a dissacharide useful for the synthetic elaboration of decarbamoyl bleomycin.
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U2 - 10.1021/jo00365a013
DO - 10.1021/jo00365a013
M3 - Article
AN - SCOPUS:0022458335
SN - 0022-3263
VL - 51
SP - 2927
EP - 2932
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 15
ER -