213895-44-4

Upstream product

• 74124-79-1 di(succinimido) carbonate 
• 213895-37-5 2,5-di-O-benzyl-3,4-O-isopropylidene-L-mannaric acid 
• 153059-35-9 1,2:3,4:5,6-tri-O-isopropylidene-L-mannitol 
• 213895-35-3 2,5-di-O-benzyl-1,6-di-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-L-mannitol 
• 213895-34-2 1,6-di-O-tert-butyldimethylsilyl-3,4-O-isopropylidene-L-mannitol 
• 213895-36-4 2,5-di-O-benzyl-3,4-O-isopropylidene-L-mannitol 
• 153059-36-0 3,4-O-isopropylidene-L-mannitol 
• 294867-69-9 N₁,N₆-dimethyl-(2R,3R,4R,5R)-2,5-dibenzyloxy-3,4-dihydroxy-3,4-O-isopropylidenehexanediamide 
• 294867-67-7 N₁,N₆-dimethyl-(2R,3R,4R,5R)-2,5-dibenzyloxy-3,4-dihydroxy hexanediamide 
• 213895-58-0 2,5-di-O-benzyl-L-mannaro-1,4:3,6-di-γ-lactone 

Relevant academic research and scientific papers

Solid phase assisted synthesis of HIV-1 inhibitors. Expedient entry to unsymmetrical substitution of a C2 symmetric template

A solid phase synthesis has been developed leading up to unsymmetrical HIV-1 protease inhibitors that are not readily available by conventional solution phase chemistry (18a-g). To prepare these compounds the hydroxyl group of (1s,2r)-(-)-cis-1-phthalimido-2-indanol (3) was coupled to a Merrifield resin via a dihydropyrane linker. Cleavage of the phthalimido protecting group and reaction of the liberated amine with the bis-activated symmetrical diacid 15 resulted in the resin bound amide 16. Coupling of 16 with amino acids and amines followed by hydrolysis produced the desired unsymmetrical products 18a-g from which potent HIV-1 protease inhibitors were identified, e.g., 18e (k(i) = 0.1 nM), 18a (k(i) = 0.2 nM) and 18c (k(i) = 2 nM).

Design and synthesis of new potent C2-symmetric HIV-1 protease inhibitors. Use of L-mannaric acid as a peptidomimetic scaffold

A study on the use of derivatized carbohydrates as C2-symmetric HIV-1 protease inhibitors has been undertaken. L-Mannaric acid (6) was bis-O- benzylated at C-2 and C-5 and subsequently coupled with amino acids and amines to give C2-s