528864-97-3

Upstream product

• 528864-92-8 (4S,2'R,3'R)-3-[7'-benzyloxy-3'-(tert-butyldiphenylsilanyloxy)-2'-methylheptanoyl]-4-isopropyl-1,3-oxazolidin-2-one 
• 528864-93-9 (2R,3R)-7-(benzyloxy)-3-(tert-butyldiphenylsilyloxy)-2-methylheptanol 
• 528864-90-6 (4S,2'R,3'R)-3-(7'-benzyloxy-3'-hydroxy-2'-methylheptanoyl)-4-isopropyl-1,3-oxazolidin-2-one 
• 78999-24-3 5-benzyloxy-1-pentanal 
• 143-33-9 sodium cyanide 
• 528864-95-1 (2R,3R)-7-(benzyloxy)-3-(tert-butyldiphenylsilyloxy)-2-methylheptanol p-toluenesulfonate 

Downstream Products

• 528865-13-6 {2-[(E)-(4R,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-8-phenyl-oct-7-enyl]-[1,3]dithian-2-yl}-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methanol 
• 528865-17-0 Acetic acid (E)-(1R,2R)-1-(3-{2-[(R)-hydroxy-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl]-[1,3]dithian-2-yl}-propyl)-2-methyl-5-phenyl-pent-4-enyl ester 
• 528865-16-9 (E)-(4R,5R)-1-{2-[(R)-Hydroxy-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl]-[1,3]dithian-2-yl}-5-methyl-8-phenyl-oct-7-en-4-ol 
• 528865-01-2 (5R,6R,8E)-O-benzyl-5-(tert-butyldiphenylsilyloxy)-6-methyl-9-phenylnon-8-enol 
• 528865-06-7 (4'R,5'R,7'E)-2-[4'-(tert-butyldiphenylsilyloxy)-5'-methyl-8'-phenyl-oct-7'-en-1'-yl]-1,3-dithiane 
• 528864-99-5 (3R,4R)-8-(benzyloxy)-4-(tert-butyldiphenylsilyloxy)-3-methyloctanal 
• 528865-03-4 (5R,6R,8E)-5-(tert-butyldiphenylsilyloxy)-6-methyl-9-phenylnon-8-enol 
• 528865-04-5 (5R,6R,8E)-5-(tert-butyldiphenylsilyloxy)-6-methyl-9-phenylnon-8-enal 
• 1064663-96-2 (3R,4R)-8-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-octylideneamine 

Relevant academic research and scientific papers

Synthesis of the C1-side chain of zaragozic acid D and progress towards a total synthesis

A synthesis of a 1,3-dithiane corresponding to the C1-side chain of zaragozic acid D is described. An aldol reaction using an Evans oxazolidinone is the key step in controlling stereochemistry. Metallation of the derived dithiane monosulfoxide and coupling to an aldehyde effected construction of the C1-C7 bond. Subsequent steps are also reported, including acid-mediated ketalization resulting in formation of an advanced synthetic intermediate containing the bicyclic ketal core of the natural product.