Synthesis of new iso-C-nucleoside analogues from 2-(methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-alpha-D-altropyranosid-3-yl)ethanal.
Treatment of 2-(methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-alpha-D-altropyranosid-3-yl)ethanal with malononitrile, cyanoacetamide and 2-cyano-N-(4-methoxyphenyl)acetamide, respectively, in the presence of aluminium oxide yielded 2-cyano-4-(methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-alpha-D-altropyranosid-3-yl)crotonic acid derivatives. Cyclization with sulfur and triethylamine was performed to synthesize the 2-amino-5-(methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-alpha-D-altropyranosid-3-yl)thiophene-3-carbonic acid derivatives, which were treated with triethyl orthoformate/ammonia and triethyl orthoformate, respectively, to furnish 6-(methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-alpha-D-altropyranosid-3-yl)thieno[2.3-d]pyrimidine derivatives. Deprotection in two steps afforded 2-amino-5-(1,6-anhydro-3-deoxy-beta-D-altropyranos-3-yl)thiophene-3-carbonitrile and 6-(1,6-anhydro-3-deoxy-beta-D-altropyranos-3-yl)thieno[2.3-d]pyrimidine derivatives, respectively.
Otero
Iran
I
Institut für Chemie, Universität Rostock, D-18051 Rostock, Germany.
Feist
Holger
H
Herrera
Lidcay
L
Michalik
Manfred
M
Quincoces
José
J
Peseke
Klaus
K
D000537:Aluminum Oxide / Q000737:chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D006027:Glycosides / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013455:Sulfur / Q000737:chemistry
C502021:2-(methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxyaltropyranosid-3-yl)ethanal; D006027:Glycosides; D009570:Nitriles; D009705:Nucleosides; D011743:Pyrimidines; C476003:thienopyrimidine; D013455:Sulfur; C000945:dicyanmethane; D000537:Aluminum Oxide; C031594:2-cyanoacetamide