Tetrahedron

New syntheses of 2', 3'-dideoxy-2', 3'-di-substituted &-2'-mono-substituted uridines & adenosines by michael addition reactions

…, W Tong, JM Vial, G Remaud, J Chattopadhyaya

Index: Wu; Pathak; Tong; Vial; Remaud; Chattopadhyaya Tetrahedron, 1988 ,  vol. 44,  # 21  p. 6705 - 6722

Full Text: HTML

Citation Number: 59

Abstract

Michael addition reactions of the 3'-enesulfones 5, 6 and 18 with ammonia, primary amines (methylamine, benzylamine, glycine methyl ester), secondary amines (dimethylamine, pyrrolidine, piperidine, morpholine) and carbon-nucleophiles (sodium methylmalonate, conjugate base of nitromethane and pyrrolidin-1-cyclohexene) have been used as means to synthesize new 2', 3'-dideoxy-2', 3'-disubstituted-or 2'-substituted nucleosides. Most of ...

 Related Synthetic Route
Piperidine Structure

110-89-4

Piperidine

1-(5'-trityl-2',3'-dideoxy-3'-toluenesulfonyl-β-D-glyceropent-2-enofuranosyl)uracil Structure

119753-91-2

1-(5'-trityl-2'...

~96%

1-((2R,3S,4R,5R)-3-(piperidin-1-yl)-4-tosyl-5-((trityloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione Structure

119753-99-0

1-((2R,3S,4R,5R...

1-[2,3-epoxy-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]pyrimidine-2,4(1H,3H)-dione Structure

96253-10-0

1-[2,3-epoxy-5-...

~%

1-((2R,3S,4R,5R)-3-(piperidin-1-yl)-4-tosyl-5-((trityloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione Structure

119753-99-0

1-((2R,3S,4R,5R...

1-(5'-O-trityl-3'-deoxy-3'-(4-toluene)thio-β-D-arabinofuranosyl)uracil Structure

119753-89-8

1-(5'-O-trityl-...

~%

1-((2R,3S,4R,5R)-3-(piperidin-1-yl)-4-tosyl-5-((trityloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione Structure

119753-99-0

1-((2R,3S,4R,5R...

1-(5'-O-trityl-3'-deoxy-3'-toluenesulfonyl-β-D-arabinofuranosyl)uracil Structure

119753-90-1

1-(5'-O-trityl-...

~%

1-((2R,3S,4R,5R)-3-(piperidin-1-yl)-4-tosyl-5-((trityloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione Structure

119753-99-0

1-((2R,3S,4R,5R...

1-[2,3-di-O-(metanesulfonyl)-5-O-(triphenylmethyl)-β-D-ribofuranosyl]pyrimidine-2,4(1H,3H)-dione Structure

110524-37-3

1-[2,3-di-O-(me...

~%

1-((2R,3S,4R,5R)-3-(piperidin-1-yl)-4-tosyl-5-((trityloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione Structure

119753-99-0

1-((2R,3S,4R,5R...

1-(5'-O-trityl-3'-deoxy-3'-toluenesulfonyl-β-D-arabinofuranosyl)uracil Structure

119753-90-1

1-(5'-O-trityl-...

~73%

1-(5'-trityl-2',3'-dideoxy-3'-toluenesulfonyl-β-D-glyceropent-2-enofuranosyl)uracil Structure

119753-91-2

1-(5'-trityl-2'...

1-[2,3-epoxy-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]pyrimidine-2,4(1H,3H)-dione Structure

96253-10-0

1-[2,3-epoxy-5-...

~%

1-(5'-trityl-2',3'-dideoxy-3'-toluenesulfonyl-β-D-glyceropent-2-enofuranosyl)uracil Structure

119753-91-2

1-(5'-trityl-2'...

1-(5'-O-trityl-3'-deoxy-3'-(4-toluene)thio-β-D-arabinofuranosyl)uracil Structure

119753-89-8

1-(5'-O-trityl-...

~%

1-(5'-trityl-2',3'-dideoxy-3'-toluenesulfonyl-β-D-glyceropent-2-enofuranosyl)uracil Structure

119753-91-2

1-(5'-trityl-2'...

1-[2,3-di-O-(metanesulfonyl)-5-O-(triphenylmethyl)-β-D-ribofuranosyl]pyrimidine-2,4(1H,3H)-dione Structure

110524-37-3

1-[2,3-di-O-(me...

~%

1-(5'-trityl-2',3'-dideoxy-3'-toluenesulfonyl-β-D-glyceropent-2-enofuranosyl)uracil Structure

119753-91-2

1-(5'-trityl-2'...

1-((2R,3S,4R,5R)-3-(piperidin-1-yl)-4-tosyl-5-((trityloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione Structure

119753-99-0

1-((2R,3S,4R,5R...

~28%

1-((2R,3R,5S)-3-(piperidin-1-yl)-5-((trityloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione Structure

119753-58-1

1-((2R,3R,5S)-3...

1-[2,3-epoxy-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]pyrimidine-2,4(1H,3H)-dione Structure

96253-10-0

1-[2,3-epoxy-5-...

~%

1-((2R,3R,5S)-3-(piperidin-1-yl)-5-((trityloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione Structure

119753-58-1

1-((2R,3R,5S)-3...

1-(5'-O-trityl-3'-deoxy-3'-(4-toluene)thio-β-D-arabinofuranosyl)uracil Structure

119753-89-8

1-(5'-O-trityl-...

~96%

1-(5'-O-trityl-3'-deoxy-3'-toluenesulfonyl-β-D-arabinofuranosyl)uracil Structure

119753-90-1

1-(5'-O-trityl-...

1-[2,3-epoxy-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]pyrimidine-2,4(1H,3H)-dione Structure

96253-10-0

1-[2,3-epoxy-5-...

~%

1-(5'-O-trityl-3'-deoxy-3'-toluenesulfonyl-β-D-arabinofuranosyl)uracil Structure

119753-90-1

1-(5'-O-trityl-...

1-[2,3-di-O-(metanesulfonyl)-5-O-(triphenylmethyl)-β-D-ribofuranosyl]pyrimidine-2,4(1H,3H)-dione Structure

110524-37-3

1-[2,3-di-O-(me...

~%

1-(5'-O-trityl-3'-deoxy-3'-toluenesulfonyl-β-D-arabinofuranosyl)uracil Structure

119753-90-1

1-(5'-O-trityl-...

1-[2,3-di-O-(metanesulfonyl)-5-O-(triphenylmethyl)-β-D-ribofuranosyl]pyrimidine-2,4(1H,3H)-dione Structure

110524-37-3

1-[2,3-di-O-(me...

~%

1-(5'-O-trityl-3'-deoxy-3'-(4-toluene)thio-β-D-arabinofuranosyl)uracil Structure

119753-89-8

1-(5'-O-trityl-...

1-[2,3-epoxy-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]pyrimidine-2,4(1H,3H)-dione Structure

96253-10-0

1-[2,3-epoxy-5-...

~%

1-((2R,3R,5S)-3-morpholino-5-((trityloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione Structure

119753-59-2

1-((2R,3R,5S)-3...

1-(5'-O-trityl-3'-deoxy-3'-(4-toluene)thio-β-D-arabinofuranosyl)uracil Structure

119753-89-8

1-(5'-O-trityl-...

~%

1-((2R,3R,5S)-3-morpholino-5-((trityloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione Structure

119753-59-2

1-((2R,3R,5S)-3...

1-(5'-trityl-2',3'-dideoxy-3'-toluenesulfonyl-β-D-glyceropent-2-enofuranosyl)uracil Structure

119753-91-2

1-(5'-trityl-2'...

~%

1-((2R,3R,5S)-3-morpholino-5-((trityloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione Structure

119753-59-2

1-((2R,3R,5S)-3...

1-(5'-O-trityl-3'-deoxy-3'-toluenesulfonyl-β-D-arabinofuranosyl)uracil Structure

119753-90-1

1-(5'-O-trityl-...

~%

1-((2R,3R,5S)-3-morpholino-5-((trityloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione Structure

119753-59-2

1-((2R,3R,5S)-3...

1-[2,3-di-O-(metanesulfonyl)-5-O-(triphenylmethyl)-β-D-ribofuranosyl]pyrimidine-2,4(1H,3H)-dione Structure

110524-37-3

1-[2,3-di-O-(me...

~%

1-((2R,3R,5S)-3-morpholino-5-((trityloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione Structure

119753-59-2

1-((2R,3R,5S)-3...

1-(5'-O-trityl-3'-deoxy-3'-(4-toluene)thio-β-D-arabinofuranosyl)uracil Structure

119753-89-8

1-(5'-O-trityl-...

~%

1-((2R,3R,5S)-3-(piperidin-1-yl)-5-((trityloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione Structure

119753-58-1

1-((2R,3R,5S)-3...

1-(5'-trityl-2',3'-dideoxy-3'-toluenesulfonyl-β-D-glyceropent-2-enofuranosyl)uracil Structure

119753-91-2

1-(5'-trityl-2'...

~%

1-((2R,3R,5S)-3-(piperidin-1-yl)-5-((trityloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione Structure

119753-58-1

1-((2R,3R,5S)-3...

1-(5'-O-trityl-3'-deoxy-3'-toluenesulfonyl-β-D-arabinofuranosyl)uracil Structure

119753-90-1

1-(5'-O-trityl-...

~%

1-((2R,3R,5S)-3-(piperidin-1-yl)-5-((trityloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione Structure

119753-58-1

1-((2R,3R,5S)-3...

1-[2,3-di-O-(metanesulfonyl)-5-O-(triphenylmethyl)-β-D-ribofuranosyl]pyrimidine-2,4(1H,3H)-dione Structure

110524-37-3

1-[2,3-di-O-(me...

~%

1-((2R,3R,5S)-3-(piperidin-1-yl)-5-((trityloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione Structure

119753-58-1

1-((2R,3R,5S)-3...

1-[2,3-epoxy-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]pyrimidine-2,4(1H,3H)-dione Structure

96253-10-0

1-[2,3-epoxy-5-...

~%

1-((2R,3R,5S)-3-(pyrrolidin-1-yl)-5-((trityloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione Structure

119753-57-0

1-((2R,3R,5S)-3...

1-(5'-O-trityl-3'-deoxy-3'-(4-toluene)thio-β-D-arabinofuranosyl)uracil Structure

119753-89-8

1-(5'-O-trityl-...

~%

1-((2R,3R,5S)-3-(pyrrolidin-1-yl)-5-((trityloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione Structure

119753-57-0

1-((2R,3R,5S)-3...

1-(5'-trityl-2',3'-dideoxy-3'-toluenesulfonyl-β-D-glyceropent-2-enofuranosyl)uracil Structure

119753-91-2

1-(5'-trityl-2'...

~%

1-((2R,3R,5S)-3-(pyrrolidin-1-yl)-5-((trityloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione Structure

119753-57-0

1-((2R,3R,5S)-3...

1-(5'-O-trityl-3'-deoxy-3'-toluenesulfonyl-β-D-arabinofuranosyl)uracil Structure

119753-90-1

1-(5'-O-trityl-...

~%

1-((2R,3R,5S)-3-(pyrrolidin-1-yl)-5-((trityloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione Structure

119753-57-0

1-((2R,3R,5S)-3...

1-[2,3-di-O-(metanesulfonyl)-5-O-(triphenylmethyl)-β-D-ribofuranosyl]pyrimidine-2,4(1H,3H)-dione Structure

110524-37-3

1-[2,3-di-O-(me...

~%

1-((2R,3R,5S)-3-(pyrrolidin-1-yl)-5-((trityloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione Structure

119753-57-0

1-((2R,3R,5S)-3...


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