162517-92-2

Upstream product

• 10323-20-3 D-Arabinose 
• 162517-90-0 5-O-(tert-butyldiphenylsilyl)-D-arabinose diethyldithioacetal 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 114738-04-4 (3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol 
• 172751-32-5 5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-β-D-threo-pentofuranose-3-ulose 
• 1941-50-0 D-arabinose diethyl dithioacetal 
• 123107-60-8 5-O-(tert-butyldiphenylsilyl)-3-C-(carbomethoxymethyl)-3-deoxy-1,2-O-isopropylidene-β-D-lyxofuranose 

Downstream Products

• 162517-93-3 5-O-(tert-butyldiphenylsilyl)-3-C-(2'-O-methanesulfonyl-2'-hydroxyethyl)-3-deoxy-1,2-isopropylidene-β-D-lyxofuranose 
• 1008742-81-1 5-O-[tert-butyl(diphenyl)silyl]-3-deoxy-1,2-O-isopropylidene-3-[2-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)ethyl]-β-D-lyxofuranose 
• 1008743-37-0 5-O-[tert-butyl(diphenyl)silyl]-3-deoxy-3-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-1,2-O-(1-methylethylidene)-β-D-lyxofuranose 
• 123107-59-5 3-C-(2'-azidoethyl)-5-O-(tert-butyldiphenylsilyl)-3-deoxy-1,2-isopropylidene-β-D-lyxofuranose 
• 123107-64-2 (3S,4R)-N-benzyloxycarbonyl-3-hydroxy-4-((S)-1,2-dihydroxyethyl) piperidine 
• 123165-55-9 (1S,3S,7S,8S)-N-benzyloxycarbonyl-5,5-dimethyl-11-aza-2,4,6-trioxatricyclo<6.4.0.0^3,7>dodecane 
• 123130-05-2 (1'S,3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-(2',2'-bisthioethyl-1'-hydroxy)ethyl piperidine 
• 123130-04-1 (2S,3'S,4'R)-2-<4'-(N-benzyloxycarbonyl-3'-hydroxy)piperidyl>-2-hydroxyethyl methanesulfonate 
• 162518-00-5 (1'S,3S,4S)-N-benzyloxycarbonyl-3-benzyloxy-4-(1'-benzyloxy-2'-hydroxy)ethyl piperidine 
• 162517-99-9 (1'S,3S,4S)-N-benzyloxycarbonyl-3-benzyloxy-4-(2',2'-bisthioethyl-1'-benzyloxy)ethyl piperidine 
• 123130-06-3 (1'S,3S,4S)-N-benzyloxycarbonyl-3-benzyloxy-4-(1'-benzyloxy-2'-hydroxy-2'-O-methanesulphonyl)ethyl piperidine 
• 162517-96-6 <3S-(3α,3aα,7aα)>-N-benzyloxycarbonyl-octahydro-2-furo<2,3-c>pyridinol 
• 162601-59-4 (3S,5S)-3,5-di-O-benzylquinuclidine-3,5-diol 
• 162517-95-5 (3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-((S)-1,2-dihydroxyethyl)piperidine 

Relevant academic research and scientific papers

MATRIX METALLOPROTEINASE INHIBITORS

The present invention relates to β-hydroxy and amino substituted carboxylic acids, which act as matrix metalloprotease inhibitors, particularly diastereomerically pure β-hydroxy carboxylic acids, corresponding processes for the synthesis of and pharmaceutical compositions containing the compounds of the present invention. Compounds of the present invention are useful in the treatment of various inflammatory, autoimmune and allergic diseases, such as methods of treating asthma, rheumatoid arthritis, COPD, rhinitis, osteoarthritis, psoriatic arthritis, psoriasis, pulmonary fibrosis, wound healing disorders, pulmonary inflammation, acute respiratory distress syndrome, perodontitis, multiple sclerosis, gingivitis, atherosclerosis, neointimal proliferation, which leads to restenosis and ischemic heart failure, stroke, renal diseases, tumor metastasis, and other inflammatory disorders characterized by the over-expression and over- activation of a matrix metalloproteinase using the compounds.

Synthesis of (3S,5S)-Quinuclidine-3,5-diol and of -Octahydro-2-furopyridinol from D-Arabinose

The synthesis of (3S,5S)-quinuclidine-3,5-diol is achieved by an introduction of a 2 carbon chain at C-3 of D-arabinose, followed by joining the terminus of the chain extension to C-1 and C-5 of the sugar; the synthesis of -octahydro-2-fu

Chiral Quinuclidines (1-Azabicyclooctanes) from Sugars: Synthesis of (3S,5S)-Quinuclidine-3,5-diol from D-Arabinose

The synthesis of (3S,5S)-quinuclidine-3,5-diol from D-arabinose by two alternative ring closures is described.