61084-13-7

Upstream product

• 119680-72-7 2,3:5,6-O-dicyclohexylidene D-gulono-lactone 
• 119680-76-1 2,3:5,6-di-O-cyclohexylidene-D-mannofurano-lactone 
• 108-94-1 cyclohexanone 
• 6322-07-2 D-gulono-1,4-lactone 
• 933-40-4 cycloxexanone dimethyl ketal 

Downstream Products

• 119680-73-8 methyl 5-<<(benzyloxycarbonyl)amino>methyl>-N-(2,3:5,6-O-dicyclohexylidene-D-gulofuranosyl)isoxazolidine-3-carboxylate 
• 871360-12-2 methyl 2-((3aR,4S,5aS,8R,9aS,9bS)-4-((R)-1,2-dihydroxyethyl)octahydrospiro[[1,3]dioxolo[4,5-d]pyrano[3,2-b]pyran-2,1'-cyclohexan]-8-yl)acetate 
• 119680-73-8 C₃₂H₄₄N₂O₁₀ 

Relevant academic research and scientific papers

Synthesis of the C1–C13 fragment of eribulin mesylate

Synthesis of the C1–C13 fragment of eribulin mesylate has been accomplished. It features a highly stereoselective construction of a trans-dihydropyran framework using three key reactions: (1) Sharpless epoxidation, (2) regioselective ring opening, and (3) olefin metathesis.

Process development of halaven: Synthesis of the C1-C13 fragment from d -(-)-gulono-1,4-lactone

A 12-step kilogram-scale synthesis of the C1-C13 fragment, common to halichondrin B and the totally synthetic analogue Halaven (E7389, INN eribulin mesylate), is described. The synthesis features four crystalline intermediates which facilitates throughput, and enhances quality control of all stereogenic centers in the title compound. Georg Thieme Verlag Stuttgart. New York.

INTERMEDIATES FOR THE PREPARATION OF HALICHONDRIN B

The present invention provides macrocyclic compounds, synthesis of the same and intermediates thereto. Such compounds, and compositions thereof, are useful for treating or preventing proliferative disorders Formula (F-4).

Asymmetric Total Synthesis of (+)-Negamycin and (-)-3-Epinegamycin via Enantioselective 1,3-Dipolar Cycloaddition

Enantioselective total synthesis of (+)-negamycin and (-)-3-epinegamycin has been achieved by the introduction of asymmetry through 1,3-dipolar cycloaddition with chiral nitrones modified with carbohydrates.For the model study, the trans-isoxazolidine-3-carboxylate (+/-)-6a, obtained by 1,3-dipolar cycloaddition of the nitrone 4 with N-(benzyloxycarbonyl)allylamine (5), was converted into the hydrazide (+/-)-13 via six steps, catalytic hydrogenation of which resulted in deprotection and N-O bond cleavage at the same time, affording (+/-)-negamycin .This sequence was next applied to the synthesis of (+)-negamycin.Thus the enantioselective 1,3-dipolar cycloaddition of nitrones modified with carbohydrates, such as D- and L-gulose, D-ribose, and D-mannose derivatives, with 5 was investigated.Among these nitrones the gulosyl series proved to produce the best results.The trans adduct D-19a with 94percent ee thus obtained by using N-D-gulosylnitrone D-18 was converted into (+)-negamycin by hydrolytic removal of the chiral auxiliary followed by a similar sequence for the synthesis of (+/-)-1.Similarly, the cis adduct D-19b with 94percent ee obtained by cycloaddition with the D-gulosylnitrone D-18 was transformed into (-)-3-epinegamycin .With synthetic (+)-1 and (-)-2 in hand, antibacterial activity was examined.