475291-41-9

Upstream product

• 397870-66-5 2,2,2-Trichloro-acetimidic acid (Z)-4-benzyloxy-3-((3aR,5R,6S,6aR)-6-methoxymethoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-but-2-enyl ester 
• 184964-57-6 N-[(R)-1-benzyloxy-2-{(1R,5R,7R,8S)-3,3-dimethyl-8-methoxymethoxy-2,4,6-trioxabicyclo[3.3.0]octane-7-yl}but-3-en-2-yl]trichloroacetamide 
• 397870-68-7 4-benzyloxy-3-{(1R,5R,7R,8S)-8-methoxymethoxy-3,3-dimethyl-2,4,6-trioxabicyclo[3.3.0]octan-7-yl}but-2-enoate 
• 397870-78-9 (E)-4-benzyloxy-3-{(1R,5R,7R,8S)-8-methoxymethoxy-3,3-dimethyl-2,4,6-trioxabicyclo[3.3.0]oct-7-yl}but-2-en-1-ol 
• 397870-69-8 (Z)-4-benzyloxy-3-{(1R,5R,7R,8S)-8-methoxymethoxy-3,3-dimethyl-2,4,6-trioxabicyclo[3.3.0]oct-7-yl}but-2-en-1-ol 
• 397870-67-6 6-O-benzyl-1,2-O-isopropylidene-3-O-methoxymethyl-α-D-gluco-hexofuranose 
• 475291-30-6 6-O-benzyl-1,2-O-isopropylidene-3-O-methoxymethyl-α-D-xylo-hexofuranos-5-ulose 
• 104487-62-9 1,2-O-isopropylidene-3-O-methoxymethyl-α-D-glucofuranose 
• 100-39-0 benzyl bromide 

Relevant academic research and scientific papers

Total synthesis of (+)-myriocin and (-)-sphingofungin E from aldohexoses using overman rearrangement as the key reaction

Total synthesis starting from aldohexoses of naturally occurring α-substituted α-amino acids, (+)-myriocin (1) and (-)-sphingofungin E (2), is described. Overman rearrangement of allylic trichloroacetimidate 6E derived from D-mannose effectively generated the tetrasubstituted carbon with nitrogen, and subsequent Wittig olefination afforded the highly functionalized moiety 3 of myriocin stereoselectively. Sulfone-mediated coupling reaction of the allyl bromide 3 with C12 hydrophobic part 4 successfully constructed the carbon framework possessing E-olefin 28. Removal of the sulfone and protecting groups completed the chiral and stereoselective total synthesis of (+)-myriocin (1). A similar transformation starting from D-glucose also accomplished the total synthesis of (-)-sphingofungin E (2).