Ish K. Khanna

Arthur L. Campbell; Daniel R. Pilipauskas; Ish K. Khanna; R.Allen Rhodes

Abstract Benzyl groups are efficiently and selectively cleaved from tertiary alkylamines using β-trimethylsilylethyl chloroformate. This general method is compatible with a wide range of functionality because it does not require strong hydrolytic or acidic solvolytic conditions.

James R. Behling; Payman Farid; John R. Medich; Mike G. Scaros; Michael Lee Prunier; Richard M. Weier; Ish K. Khanna

Abstract The potent glucosidase inhibitor 1-deoxynojirimycin was synthesized from L-sorbose using a short synthesis and only one protecting group. The last step, which constituted the removal of an acetonide protecting group and an intramolecular reductive amination, was accomplished on an acidic lon-exchange resin. This provided a synthesis capable of being operated on a multi-kilogram scale.

Ish K. Khanna; Francis J. Koszyk; Michael A. Stealey; Richard M. Weier; Janet Julien; Richard A. Mueller; Shashidhar N. Rao; Lydia Swenton; Daniel P. Getman; Gary A. DeCrescenzo; Robert M. Heintz

Abstract A useful methodology for the synthesis of a number of 2-, 3- and 2,3-disubstituted deoxynojirimycin analogs is reported. It has been found that the epoxides in stereoselectively synthesized N-carboalkoxy-2,3-anhydro-1-deoxymannojirimycins (4 and 5) react with N-, S- and F- nucleophiles to give a mixture of gluco and altro products. The 3-azido altro compound (12b) yields the desired gluco derivative (40) by oxidation, in situ epimerization at C-3, followed by stereoselective reduction of the carbonyl group. The azido intermediate (12a) affords the 2,3-diazido gluco compound (51) by double inversion at C-3. Attempts have been made to understand the factors contributing to the opening of epoxides (4, 5 and 9) by different nucleophiles.

Ish K. Khanna; Richard M. Weier; Janet Julien; Richard A. Mueller; David C. Lankin; Lydia Swenton

The regio- and stereoselective synthesis of the title compounds 3 and 4 has been accomplished starting with deoxynojirimycin. The factors affecting the stereochemical outcome of Grignard addition to the key carbonyl intermediate are discussed.

Ish K. Khanna; Richard M. Weier

Abstract The addition of Grignard reagents to 5-acylimidazopyridinium salts gives 4-substituted 5-acyl-4,5-dihydroimidazopyridines. This reaction was utilized t

Arthur L. Campbell; Ish K. Khanna

Abstract Regioselective metallation and alkylation/acylation of 2-aryl-1,3-dioxanes was achieved in high yield.

John J. Talley; Thomas D. Penning; Paul W. Collins; Donald J. Rogier; James W. Malecha; Julie M. Miyashiro; Stephen R. Bertenshaw; Ish K. Khanna; Matthew J. Graneto; Roland S. Rogers; Jeffery S. Carter

John J. Talley; Thomas D. Penning; Paul W. Collins; Donald J. Rogier; James W. Malecha; Julie M. Miyashiro; Stephen R. Bertenshaw; Ish K. Khanna; Matthew J. Graneto; Roland S. Rogers; Jeffery S. Carter; Stephen H Docter; Stella S. Yu

John J. Talley; James W. Malecha; Stephen R. Bertenshaw; Matthew J. Graneto; Jeffery S. Carter; Jinglin Li; Srinivasan Nagarajan; David L. Brown; Donald J. Rogier; Thomas D. Penning; Ish K. Khanna; Xiangdong Xu; Richard M. Weier

Ashok S. Naraian; Michael Clare; Paul W. Collins; Joyce Zuowu Crich; Rajesh Ballwin Devraj; Daniel L. Flynn; Lifeng Geng; Matthew J. Graneto; Cathleen E Hanau; Gunnar J. Hanson; Susan J. Hartmann; Michael St. Charles Hepperle; He Huang; Francis J. Koszyk; Shuyuan Liao; Suzanne Metz; Richard A. Partis; Thao D. Red Bud Perry; Shashidhar N. Rao; Shaun Raj Selness; Michael S. South; Michael A. Stealey; John J. Talley; Michael L. Vazquez; Richard M. Weier; Xiangdong Xi; Ish K. Khanna; Yi Yu