TY - JOUR
T1 - Synthesis of the Carbohydrate Moiety of Bleomycin. 1,3,4,6-Tetra-O-substituted L-Gulose Derivatives
AU - Katano, Kiyoaki
AU - Chang, Pei In
AU - Millar, Alan
AU - Pozsgay, Vince
AU - Minster, David K.
AU - Ohgi, Tadaaki
AU - Hecht, Sidney M.
PY - 1985/12
Y1 - 1985/12
N2 - To facilitate the synthesis of the carbohydrate moiety of bleomycin [2-O-(3-O-carbamoyl-α-D-manno-pyranosyl)-L-gulopyranose] and its subsequent attachment to the remainder of the bleomycin molecule in a regio- and stereoselective fashion, a number of suitably protected gulose derivatives were prepared and their chemistry was studied. Key intermediates included 1,6-anhydro-3,4-di-O-benzyl-β-L-gulopyranose (12), 1,6-di-O-acetyl-3,4-di-O-benzyl-β-L-gulopyranose (24), benzyl 3,4,6-tri-O-benzyl-β-L-gulopyranoside (27), and 3,4-di-O-benzyl-1,6-dideoxy-1,6-(1-hydrazinyl-2-ylidene)-β-D-glucodialdehydo-1,5-pyranose (28).
AB - To facilitate the synthesis of the carbohydrate moiety of bleomycin [2-O-(3-O-carbamoyl-α-D-manno-pyranosyl)-L-gulopyranose] and its subsequent attachment to the remainder of the bleomycin molecule in a regio- and stereoselective fashion, a number of suitably protected gulose derivatives were prepared and their chemistry was studied. Key intermediates included 1,6-anhydro-3,4-di-O-benzyl-β-L-gulopyranose (12), 1,6-di-O-acetyl-3,4-di-O-benzyl-β-L-gulopyranose (24), benzyl 3,4,6-tri-O-benzyl-β-L-gulopyranoside (27), and 3,4-di-O-benzyl-1,6-dideoxy-1,6-(1-hydrazinyl-2-ylidene)-β-D-glucodialdehydo-1,5-pyranose (28).
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U2 - 10.1021/jo00350a073
DO - 10.1021/jo00350a073
M3 - Article
AN - SCOPUS:0022375105
SN - 0022-3263
VL - 50
SP - 5807
EP - 5815
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 26
ER -