4-(2'-O-acetyl-3'-deoxy-3'-isothiocyanato-α-L-threofuranosyl)-1,3-dihydro-3-methyl-1-p-tolyl-2H-imidazole-2-thione

Base Information

Chemical Name:4-(2'-O-acetyl-3'-deoxy-3'-isothiocyanato-α-L-threofuranosyl)-1,3-dihydro-3-methyl-1-p-tolyl-2H-imidazole-2-thione
CAS No.:426819-14-9
Molecular Formula:C₁₈H₁₉N₃O₃S₂
Molecular Weight:389.499
Hs Code.:

Synonyms:4-(2'-O-acetyl-3'-deoxy-3'-isothiocyanato-α-L-threofuranosyl)-1,3-dihydro-3-methyl-1-p-tolyl-2H-imidazole-2-thione

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Chemical Property of 4-(2'-O-acetyl-3'-deoxy-3'-isothiocyanato-α-L-threofuranosyl)-1,3-dihydro-3-methyl-1-p-tolyl-2H-imidazole-2-thione

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Technology Process of 4-(2'-O-acetyl-3'-deoxy-3'-isothiocyanato-α-L-threofuranosyl)-1,3-dihydro-3-methyl-1-p-tolyl-2H-imidazole-2-thione

There total 5 articles about 4-(2'-O-acetyl-3'-deoxy-3'-isothiocyanato-α-L-threofuranosyl)-1,3-dihydro-3-methyl-1-p-tolyl-2H-imidazole-2-thione 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: 90.0%

: 6160-65-2
1,1'-Thiocarbonyldiimidazole

: 426819-06-9
4-(2'-O-acetyl-3'-amino-3'-deoxy-α-L-threofuranosyl)-1,3-dihydro-3-methyl-1-p-tolyl-2H-imidazole-2-thione

: 426819-14-9
4-(2'-O-acetyl-3'-deoxy-3'-isothiocyanato-α-L-threofuranosyl)-1,3-dihydro-3-methyl-1-p-tolyl-2H-imidazole-2-thione

Guidance literature:: In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/jo0110303

Reference yield:

: 426818-85-1
4-(3'-azido-3'-deoxy-α-L-threofuranosyl)-1,3-dihydro-3-methyl-1-p-tolyl-2H-imidazole-2-thione

: 426819-14-9
4-(2'-O-acetyl-3'-deoxy-3'-isothiocyanato-α-L-threofuranosyl)-1,3-dihydro-3-methyl-1-p-tolyl-2H-imidazole-2-thione

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / pyridine / 0 °C

2: 66 percent / H₂ / Pd/C / methanol / 6 h / 20 °C / 760.05 Torr

3: 90 percent / CH₂Cl₂ / 2 h / 20 °C

With pyridine; hydrogen; palladium on activated charcoal; In methanol; dichloromethane;
DOI:10.1021/jo0110303

Reference yield:

: 4-((2S,3R,4R)-3,4-Dihydroxy-tetrahydro-furan-2-yl)-3-methyl-1-p-tolyl-1,3-dihydro-imidazole-2-thione

: 426819-14-9
4-(2'-O-acetyl-3'-deoxy-3'-isothiocyanato-α-L-threofuranosyl)-1,3-dihydro-3-methyl-1-p-tolyl-2H-imidazole-2-thione

Guidance literature:: Multi-step reaction with 5 steps

1.1: 70 percent / SO₂Cl₂; Et₃N / ethyl acetate / 3.5 h / 0 °C

2.1: sodium azide / dimethylformamide / 2 h / 20 °C

2.2: 74 percent / H₂SO₄ / H₂O / 0.5 h / 20 °C

3.1: 100 percent / pyridine / 0 °C

4.1: 66 percent / H₂ / Pd/C / methanol / 6 h / 20 °C / 760.05 Torr

5.1: 90 percent / CH₂Cl₂ / 2 h / 20 °C

With pyridine; sodium azide; sulfuryl dichloride; hydrogen; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo0110303