154494-79-8Relevant academic research and scientific papers
A novel method for deprotection of N-9-phenylfluoren-9-yl group using iodine catalyst: Simple synthesis of (2S, 3R, 4R)-3,4-dihydroxyproline
Kim, Jin Hyo,Lee, Woo Song,Yang, Min Suk,Lee, Sang Gyeong,Park, Ki Hun
, p. 614 - 616 (1999)
Iodine was found to be an efficient catalyst for the deprotection of the N-phenylfluoren-9-yl (Pf) group in tertiary amine and promote an intramolecular amination. A facile and economical synthesis of (2S,3R,4R)- 3,4-dihydroxyproline was accomplished via iodine promoted cyclization and deprotection.
Chirospecific synthesis of 1,4-dideoxy-1,4-imino-D-arabinitol and 1,4-dideoxy-1,4-immo-L-xylitol via one-pot cyclisation
Kim, Jin Hyo,Yang, Min Suk,Lee, Woo Song,Park, Ki Hun
, p. 2877 - 2880 (2007/10/03)
The multi-protected compounds 4 and 5 were treated with 20% iodine in methanol to give 1,4-dideoxy-1,4-imino-D-arabinitol 1 and 1,4-dideoxy-1,4-imino-L-xylitol 2 directly. Iodine was an efficient catalyst for deprotection of O-isopropylidene, O-(tert-butyldimethylsilyl), N-(9-phenylfluoren-9-yl) and N-benzyloxycarbonyl groups, resulting in intramolecular cyclisation.
Efficient cleavage of terminal acetonide group: Chirospecific synthesis of 2,5-Dideoxy-2,5-Imino-D-Mannitol
Park, Ki Hun,Yoon, Yong Jin,Lee, Sang Gyeong
, p. 9737 - 9740 (2007/10/02)
Dowex 50W-X8 was efficient catalyst for selective cleavage of terminal actonide including acid-sensitive multifunctional groups. A facile and economically synthesis of DMDP (2,5-dideoxy-2,5-imino-D-mannitol) is described via selective hydrolysis and intramolecular nucleophilic amination.
Enantioselective synthesis of (1R,4S)-1-amino-4-(hydroxymethyl)-2- cyclopentene, a precursor for carbocyclic nucleoside synthesis
Ki Hun Park,Rapoport
, p. 394 - 399 (2007/10/02)
(1R,4S)-1-Amino-4-(hydroxymethyl)-2-cyclopentene, an important precursor for the synthesis of carbocyclic nucleosides, has been prepared from D- glucono-δ-lactone in enantiomerically pure form (er > 99/1). The synthesis proceeded from the lactone via the diisopropylidene-2-amino-2-deoxymannonate and hydrolysis of the terminal isopropylidene group. Selective oxidation of the primary alcohol and esterification gave the corresponding mannarate which was deoxygenated at C5. Further transformations by regiospecific eliminative cleavage of the ketal and hydrogenation gave dimethyl (2S,3R)-2-amino-3- hydroxyadipate. Dieckmann cyclization through specific carbanion formation at C5 led to the aminohydroxy(methoxycarbonyl)cyclopentanone which was readily converted in a series of high-yielding steps to the target cyclopentene. Throughout the synthesis, stereo- and regioselectivities were strongly influenced by the sterically demanding 9-phenyl-9-fluorenyl protecting group on nitrogen.
