240127-86-0

Upstream product

• 240127-84-8 (S)-3-(Benzyl-methyl-amino)-3-((2R,3R)-3-methyl-oxiranyl)-propionic acid methyl ester 
• 139686-29-6 methyl (4R,5R)-(4,5)-epoxy-2(E)-hexenoate 
• 103-67-3 benzyl-methyl-amine 

Downstream Products

• 54826-92-5 (5R,6S)-5,6-dihydro-5-hydroxy-6-methylpyran-2-one 

Relevant academic research and scientific papers

The reaction of (4R,5R)- and (4S,5S)-4,5-epoxy-2(E)-hexenoates and secondary amines

A reaction of methyl (4R,5R)-4,5-epoxy-2(E)-hexenoate 1 with N-benzylmethylamine gave a diastereomerically pure methyl (4R,5R)-4,5-epoxy-(3S)-N-benzylmethylamino hexanoate 6 and methyl (4S,5R)-4-N-benzylmethylamino-5-hydroxy-2(E)-hexenoate 7. The former was chemoenzymatically converted to (-)-osmundalactone 11, which is an aglycone of osmundalin. On the other hand, the directly conjugated addition of dimethylamine to methyl (4S,5S)-4,5-epoxy-2(E)-hexenoate 1 followed by treatment with MeOH at 40°C exclusively provided methyl (4R,5S)-4-dimethylamino-5-hydroxy-2(E)-hexenoate 16, which was converted into L-(-)-forosamine 18.

The reaction of 4,5-epoxy-2(E)-hexenoate and secondary amines, total synthesis of (-)-osmundalactone and (-)-forosamine

A reaction of methy (4R,5R)-4,5-epoxy-2(E)-hexenoate (1) with N- methylbenzylamine gave a diastereomerically pure (3S,4R,5R)-7 and (4S,5R)-8. The former was chemoenzymatically converted to (-)-osmundalactone (12) which is an aglycone of osmundalin. On the other hand, direct conjugated addition of dimethylamine to methyl (4S,5S)-4,5-epoxy-2(E)-hexenoate (1) followed by treatment with MeOH at 40°C exclusively provided (4R,5S)-17 which was Converted into L-forosamine (19).