214619-41-7

Upstream product

• 133473-09-3 methyl 2-[(9-phenylfluoren-9-yl)amino]-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannonate 
• 154494-79-8 methyl 2-deoxy-3,4-O-isopropylidene-2-[(9-phenyl-9-fluorenyl)-amino]-D-mannonate 

Downstream Products

• 214619-39-3 Methanesulfonic acid (4R,5R)-5-[(R)-2-hydroxy-1-(9-phenyl-9H-fluoren-9-ylamino)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 404369-23-9 methyl (2S,3S)-3-(tert-butyldimethylsilyl)oxy-5-hydroxy-2-[(9-phenyl-9-fluorenyl)-amino]-pentanoate 
• 404369-24-0 trans-3-O-(tert-butyldimethylsilyl)-1-(9-phenyl-9-fluorenyl)-L-proline methyl ester 
• 404369-21-7 methyl (2S,3S)-3-(tert-butyldimethylsilyl)oxy-2-[(9-phenyl-9-fluorenyl)-amino]-4-pentenoate 
• 404369-19-3 methyl 2-deoxy-3,4-O-isopropylidene-5-iodo-2-[(9-phenyl-9-fluorenyl)-amino]-D-lyxonate 
• 404369-20-6 methyl (2S,3S)-3-hydroxy-2-[(9-phenyl-9-fluorenyl)-amino]-4-pentenoate 
• 404369-25-1 trans-3-hydroxy-1-(9-phenyl-9-fluorenyl)-L-prolinol 
• 214619-42-8 methyl 2-deoxy-3,4-O-isopropylidene-5-O-methanesulfonyl-2-[(9-phenyl-9-fluorenyl)-amino]-D-lyxonate 

Relevant academic research and scientific papers

Efficient synthesis of 3-hydroxyprolines and 3-hydroxyprolinols from sugars

trans-3-Hydroxy-L-proline 1, trans-3-hydroxy-L-prolinol 2, cis-3-hydroxy-D-proline 3, and cis-3-hydroxy-D-prolinol 4 have been prepared in enantiomerically pure form with chirospecific manner. Key intermediates, 2-amino-3-hydroxy-4-pentenoate 9 and 17, were obtained from D-glucono-δ-lactone and L-gulonic acid γ-lactone via a simultaneous dealkoxyhalogenation.

A novel method for deprotection of N-9-phenylfluoren-9-yl group using iodine catalyst: Simple synthesis of (2S, 3R, 4R)-3,4-dihydroxyproline

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

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.