Solution-phase library synthesis of furanoses.
The solution-phase synthesis of amido-, urea-, and aminofuranoses was achieved. Alkylated furanose aldehydes were treated with primary amines in the presence of sodium triacetoxyborohydride to give secondary amines. Subsequent acylation with acid chlorides and isocyanates afforded amidofuranoses and ureafuranoses, respectively. Second, reductive amination of furanose aldehydes with secondary amines yielded tertiary amines. The resulting acetonides were treated with alcohols in the presence of acid to yield mixed acetals. In the library syntheses, functionalized scavenger resins were used in the purification of intermediates and products.
Krueger
Elaine B
EB
Discovery Partners International, ChemRx Division, 385 Oyster Point Boulevard, Suite 1, South San Francisco, California 94080, USA.
Hopkins
Thutam P
TP
Keaney
Meghan T
MT
Walters
Michael A
MA
Boldi
Armen M
AM
D000080:Acetals / Q000138:chemical synthesis; D000586:Amination; D000588:Amines / Q000737:chemistry; D002241:Carbohydrates / Q000138:chemical synthesis; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D005663:Furans / Q000138:chemical synthesis; D010429:Pentoses / Q000138:chemical synthesis*; D012117:Resins, Synthetic / Q000737:chemistry; D012996:Solutions; D013237:Stereoisomerism
D000080:Acetals; D000588:Amines; D002241:Carbohydrates; D005663:Furans; D010429:Pentoses; D012117:Resins, Synthetic; D012996:Solutions