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3H-Pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,19,20,21(4H,8H,23H)-pentone, 15-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(1E)-2-[(1R,3R,4R)-4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-3-methoxycyclohexyl]-1-methylethenyl]-5,6,11,12,13,14,15,16,17,18,24,25,26,26a-tetradecahydro-5-hydroxy-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propen-1-yl)-, (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,26aS)- synthesis

1synthesis methods
5H-1,3-Dioxolo[4,5-f]pyrido[2,1-c][1,4]oxaazacyclotricosine-15,21,27(4H,6H,21aH)-trione, 7-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-19-[(1E)-2-[(1R,3R,4R)-4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-3-methoxycyclohexyl]-1-methylethenyl]-7,8,9,10,11,14,16,17,18,19,22,23,24,25-tetradecahydro-17-hydroxy-6,8-dimethoxy-2,2,4,10,12,18-hexamethyl-14-(2-propen-1-yl)-, (4R,6S,7R,8S,10S,12E,14R,17S,18R,19S,21aS)-

197250-10-5
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3H-Pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,19,20,21(4H,8H,23H)-pentone, 15-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(1E)-2-[(1R,3R,4R)-4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-3-methoxycyclohexyl]-1-methylethenyl]-5,6,11,12,13,14,15,16,17,18,24,25,26,26a-tetradecahydro-5-hydroxy-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propen-1-yl)-, (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,26aS)-

197250-11-6
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Yield:197250-11-6 100%

Reaction Conditions:

with 3,3-dimethyldioxirane in acetone at -50 - -26; for 2.16667 h;Oxidation;fragmentation;

References:

Ireland, Robert E.;Liu, Longbin;Roper, Thomas D.;Gleason, James L. [Tetrahedron,1997,vol. 53,# 39,p. 13257 - 13284]