2-[1-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-5-cyano-1H-imidazol-4-ylsulfanyl]-acetamide

Base Information

Chemical Name:2-[1-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-5-cyano-1H-imidazol-4-ylsulfanyl]-acetamide
CAS No.:374081-62-6
Molecular Formula:C₃₂H₃₂N₄O₅S
Molecular Weight:584.696
Hs Code.:

Synonyms:2-[1-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-5-cyano-1H-imidazol-4-ylsulfanyl]-acetamide

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Chemical Property of 2-[1-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-5-cyano-1H-imidazol-4-ylsulfanyl]-acetamide

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Technology Process of 2-[1-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-5-cyano-1H-imidazol-4-ylsulfanyl]-acetamide

There total 9 articles about 2-[1-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-5-cyano-1H-imidazol-4-ylsulfanyl]-acetamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 50.0%

: 758-08-7
Thioglycolamide

: 1093277-89-4
C₃₀H₂₈IN₃O₄

: 374081-62-6
2-[1-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-5-cyano-1H-imidazol-4-ylsulfanyl]-acetamide

Guidance literature:: With potassium carbonate; In N,N-dimethyl-formamide; at 60 ℃;
DOI:10.1016/j.tet.2008.09.011

Reference yield: 50.0%

: 758-08-7
Thioglycolamide

: 374081-61-5
3-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-5-bromo-3H-imidazole-4-carbonitrile

: 374081-62-6
2-[1-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-5-cyano-1H-imidazol-4-ylsulfanyl]-acetamide

Guidance literature:: With potassium carbonate;
DOI:10.1021/ol0165443

Reference yield:

: 437614-21-6
4,5-dibromo-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole

: 374081-62-6
2-[1-((2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-5-cyano-1H-imidazol-4-ylsulfanyl]-acetamide

Guidance literature:: Multi-step reaction with 6 steps

1: 100 percent / NH₃ / methanol / 3 h / 100 °C

2: 87 percent / NaH; tetrabutylammonium iodide / tetrahydrofuran / 6 h / 0 - 20 °C

3: ethylmagnesium bromide / diethyl ether / 23 h / 20 °C

4: hydroxylamine hydrochloride; NaHCO₃ / ethanol; H₂O / 2 h / 20 °C

5: 90 percent / acetic anhydride / 3 h / Heating

6: K₂CO₃ / dimethylformamide / 55 °C

With ethylmagnesium bromide; hydroxylamine hydrochloride; ammonia; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; ethanol; water; N,N-dimethyl-formamide;
DOI:10.1021/jo0255476