475291-35-1

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 386765-92-0 methyl (4S,5R)-5-[(E,R)-1-benzyloxy-5-hydroxypent-3-en-1-yl]-4-(4-methoxybenzyloxymethyl)-2-oxooxazolidine-4-carboxylate 
• 7757-38-2 2,3,5,6-di-O-isopropylidene-D-mannofuranose 
• 79241-07-9 (R)-4-((2S,3R)-3-(benzyloxy)-2,3-dihydrofuran-2-yl)-2,2-dimethyl-1,3-dioxolan 
• 386765-89-5 1-ethyl 8-methyl (E,5R,6R,7S)-5-benzyloxy-6-hydroxy-7-(4-methoxybenzyloxymethyl)-7-(trichloroacetamido)oct-2-enedioate 
• 386765-87-3 methyl (S)-2-[(2R,3R,5S)-3-benzyloxy-5-methoxyoxolan-2-yl]-3-(4-methoxybenzyloxy)-2-(trichloroacetamido)propanoate 
• 386765-82-8 2,2,2-Trichloro-acetimidic acid (E)-3-((2R,3R,5S)-3-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-4-(4-methoxy-benzyloxy)-but-2-enyl ester 
• 184964-62-3 (E)-3-[(2R,3R,5S)-3-benzyloxy-5-methoxyoxolan-2-yl]-4-(4-methoxybenzyloxy)but-2-en-1-ol 
• 386765-75-9 methyl 3-O-benzyl-6-O-(4-methoxybenzyl)-2-deoxy-α-D-arabino-hexofuranoside 
• 386765-77-1 methyl 3-O-benzyl-6-O-(4-methoxybenzyl)-2-deoxy-α-D-threo-hexofuranos-5-uloside 
• 386765-73-7 methyl 3-O-benzyl-2-deoxy-α-D-arabino-hexofuranoside 
• 68144-11-6 1,4-anhydro-2-deoxy-5,6-O-isopropylidene-D-arabinohex-1-enitol 
• 6160-67-4 (D)-mannose diacetonide 
• 475291-27-1 (S)-2-((2R,3R,5S)-3-Benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-3-(4-methoxy-benzyloxy)-2-(2,2,2-trichloro-acetylamino)-propionic acid 

Downstream Products

• 386765-98-6 (4S,5R)-5-[(E)-(R)-6-Benzenesulfonyl-1-benzyloxy-10-(2-hexyl-[1,3]dioxolan-2-yl)-dec-3-enyl]-4-(4-methoxy-benzyloxymethyl)-2-oxo-oxazolidine-4-carboxylic acid methyl ester 
• 475291-38-4 (4S,5R)-5-[(E)-(R)-6-Benzenesulfonyl-1-benzyloxy-10-(2-hexyl-[1,3]dioxolan-2-yl)-dec-3-enyl]-4-(4-methoxy-benzyloxymethyl)-2-oxo-oxazolidine-4-carboxylic acid 
• 386765-94-2 methyl (4S,5R)-5-[(E,R)-1-benzyloxy-5-bromopent-3-en-1-yl]-4-(4-methoxybenzyloxymethyl)-2-oxooxazolidine-4-carboxylate 

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).

Stereoselective total synthesis of (+)-myriocin from D-mannose

The stereoselective total synthesis of myriocin 1 from D-mannose is described; the carbon framework with three contiguous chiral centers including a tetra-substituted carbon with nitrogen was effectively constructed using Overman rearrangement as the key