118317-85-4

Upstream product

• 118299-05-1 (2E)-2,3-Dideoxy-2-methyl-4,6-di-O-methyl-7,8-O-(1-methylethylidene)-5-O-(phenylmethyl)-D-galacto-oct-2-enonic acid methyl ester 
• 126502-47-4 (E)-(4S,5R,6S,7R)-5-Benzyloxy-7,8-dihydroxy-4,6-dimethoxy-2-methyl-oct-2-enoic acid methyl ester 
• 126502-46-3 2,4-Di-O-methyl-5,6-O-(1-methylethylidene)-3-O-(phenylmethyl)-D-galactol 
• 126502-45-2 2,4-Di-O-methyl-3-O-(phenylmethyl)-D-galactol 
• 126502-46-3 (2S,3R,4S)-3-Benzyloxy-4-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,4-dimethoxy-butan-1-ol 
• 126502-45-2 (3S,4R,5S)-4-Benzyloxy-3,5-dimethoxy-hexane-1,2,6-triol 
• 118298-97-8 Methyl 6-O-<(1,1-dimethylethyl)dimethylsilyl>-2,4-di-O-methyl-3-O-(phenylmethyl)-β-D-galactopyranoside 
• 118298-99-0 Methyl 6-Deoxy-6-iodo-2,4-di-O-methyl-3-O-(phenylmethyl)-β-D-galactopyranoside 
• 118298-98-9 Methyl 2,4-di-O-methyl-3-O-(phenylmethyl)-β-D-galactopyranoside 
• 118299-00-6 5,6-Dideoxy-2,4-di-O-methyl-3-O-(phenylmethyl)-L-arabino-hex-5-enose 
• 118299-06-2 (E)-(4S,5R,6R)-5-Benzyloxy-4,6-dimethoxy-2-methyl-7-oxo-hept-2-enoic acid methyl ester 
• 2605-68-7 methyl 2-(triphenylphosphoranylidene)propionate 
• 118299-04-0 2,4-Di-O-methyl-5,6-O-(1-methylethylidene)-3-O-(phenylmethyl)-D-galactose 
• 118299-05-1 (E)-(4S,5R,6S)-5-Benzyloxy-6-(2,2-dimethyl-[1,3]dioxolan-4-yl)-4,6-dimethoxy-2-methyl-hex-2-enoic acid methyl ester 

Relevant academic research and scientific papers

Stereoselective routes to the C10-C19 fragment of FK-506

D-Galactose was used as a starting material to reach the titled system. The key elements of one of the syntheses involved directed homogeneous hydrogenation and diastereoselective lactonization reactions (see 26 → 6 and 6 → 7). In another synthetic route directed catalytic hydrogenation was used to fashion 34 where the end groups were already differentiated.