397870-72-3

Upstream product

• 100-39-0 benzyl bromide 
• 397870-70-1 N-[(R)-2-Benzyloxy-1-hydroxymethyl-1-((3aR,5R,6S,6aR)-6-methoxymethoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl]-2,2,2-trichloro-acetamide 
• 475291-40-8 N-[(R)-2-Benzyloxy-1-formyl-1-((3aR,5R,6S,6aR)-6-methoxymethoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl]-2,2,2-trichloro-acetamide 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 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 
• 397870-69-8 (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 
• 77-76-9 2,2-dimethoxy-propane 
• 475291-33-9 (E)-(4S,5R,6R,7R)-8-Benzyloxy-4,5,6-trihydroxy-7-hydroxymethyl-7-(2,2,2-trichloro-acetylamino)-oct-2-enoic acid ethyl ester 

Downstream Products

• 397870-64-3 tert-butyl N-[(E,2S,3R,4R,5S)-2-benzyloxymethyl-8-bromo-1,3:4,5-bis(isopropylidenedioxy)oct-6-en-2-yl]carbamate 
• 397870-73-4 tert-butyl N-[(E,2S,3R,4R,5S)-2-benzyloxymethyl-8-hydroxy-1,3:4,5-bis(isopropylidenedioxy)oct-6-en-2-yl]carbamate 
• 475291-43-1 Methanesulfonic acid (E)-3-[(4S,5R)-5-((4R,5S)-5-benzyloxymethyl-5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-allyl ester 
• 397870-74-5 ((4R,5S)-4-{(4R,5S)-5-[(E)-4-Benzenesulfonyl-8-(2-hexyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-5-yl)-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Total synthesis of sphingofungin E from D-glucose.

[reaction: see text] Total synthesis of sphingofungin E (1) is described. Overman rearrangement of an allylic trichloroacetimidate derived from diacetone-D-glucose generated tetra-substituted carbon with nitrogen, and subsequent Wittig olefination afforde

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).