158356-08-2

Upstream product

• 158356-07-1 N-((S)-1-Formyl-1-{(4R,5R)-5-[2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-ethyl)-benzamide 
• 158356-06-0 N-((S)-1-Hydroxymethyl-1-{(4R,5R)-5-[2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-ethyl)-benzamide 
• 77-76-9 2,2-dimethoxy-propane 
• 2186-92-7 p-Anisaldehyde dimethyl acetal 
• 186581-53-3 diazomethane 
• 1054637-94-3 (S)-2-Benzoylamino-2-{(4R,5R)-5-[2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-3-methoxymethoxy-propionic acid 

Downstream Products

• 158356-12-8 N-benzoylanhydromyriocin 
• 158356-13-9 N-[(3S,4R,5R)-4-Hydroxy-3-hydroxymethyl-2-oxo-5-((Z)-10-oxo-hexadec-2-enyl)-tetrahydro-furan-3-yl]-benzamide 
• 37836-36-5 Z-myriocin 
• 35891-70-4 myriocin 

Relevant academic research and scientific papers

Total Syntheses of Myriocin and Z-Myriocin, Two Potent Immunosuppressants, from 2-Deoxy-D-Glucose

Total syntheses of myriocin (thermozymocidin, ISP-1, 21) and its analog, Z-myriocin (22), which showed potent immunosuppressive activity, were accomplished starting from 2-deoxy-D-glucose by employing a modified Darzen reaction as a key reaction.The stereoselectivity of the modified Darzen reaction for six-membered cyclic ketones was discussed on the basis of physicochemical evidence including the conformational analyses of the cyclic ketones based on molecular mechanics calculation.

Total synthesis of a novel immunosuppressant, myriomicin (thermozymocidin, ISP-I), and Z-myriocin

Myriocin (thermozymocidin, ISP-I), which was known to exhibit several interesting biological properties such as potent immunosuppressive and antifungal activities, and a new analog Z-myriocin were synthesized from 2-deoxy-D-glucose. This synthetic pathway comprises a stereoselective formation of the chiral α,α-disubstituted amino acid structure in myriocin and Z-myriocin from the isopropylidene six-membered ketone by using a modified Darzen reaction as its key step.