N,N'-bis[2-O-acetyl-1,3-dideoxy-1-(1',3'-dihydro-3'-methyl-1'-p-tolyl-2'H-imidazole-2'-thioxo-4'-yl)-α-L-threofuranos-3-yl]thiourea

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Chemical Name:N,N'-bis[2-O-acetyl-1,3-dideoxy-1-(1',3'-dihydro-3'-methyl-1'-p-tolyl-2'H-imidazole-2'-thioxo-4'-yl)-α-L-threofuranos-3-yl]thiourea
CAS No.:426819-18-3
Molecular Formula:C₃₅H₄₀N₆O₆S₃
Molecular Weight:736.937
Hs Code.:

Synonyms:N,N'-bis[2-O-acetyl-1,3-dideoxy-1-(1',3'-dihydro-3'-methyl-1'-p-tolyl-2'H-imidazole-2'-thioxo-4'-yl)-α-L-threofuranos-3-yl]thiourea

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Chemical Property of N,N'-bis[2-O-acetyl-1,3-dideoxy-1-(1',3'-dihydro-3'-methyl-1'-p-tolyl-2'H-imidazole-2'-thioxo-4'-yl)-α-L-threofuranos-3-yl]thiourea

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Technology Process of N,N'-bis[2-O-acetyl-1,3-dideoxy-1-(1',3'-dihydro-3'-methyl-1'-p-tolyl-2'H-imidazole-2'-thioxo-4'-yl)-α-L-threofuranos-3-yl]thiourea

There total 6 articles about N,N'-bis[2-O-acetyl-1,3-dideoxy-1-(1',3'-dihydro-3'-methyl-1'-p-tolyl-2'H-imidazole-2'-thioxo-4'-yl)-α-L-threofuranos-3-yl]thiourea 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: 93.0%

: 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

: 426819-18-3
N,N'-bis[2-O-acetyl-1,3-dideoxy-1-(1',3'-dihydro-3'-methyl-1'-p-tolyl-2'H-imidazole-2'-thioxo-4'-yl)-α-L-threofuranos-3-yl]thiourea

Guidance literature:: In acetone; at 40 ℃; for 12h;
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

: 426819-18-3
N,N'-bis[2-O-acetyl-1,3-dideoxy-1-(1',3'-dihydro-3'-methyl-1'-p-tolyl-2'H-imidazole-2'-thioxo-4'-yl)-α-L-threofuranos-3-yl]thiourea

Guidance literature:: Multi-step reaction with 6 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

6.1: 93 percent / acetone / 12 h / 40 °C

With pyridine; sodium azide; sulfuryl dichloride; hydrogen; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone;
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

: 426819-18-3
N,N'-bis[2-O-acetyl-1,3-dideoxy-1-(1',3'-dihydro-3'-methyl-1'-p-tolyl-2'H-imidazole-2'-thioxo-4'-yl)-α-L-threofuranos-3-yl]thiourea

Guidance literature:: Multi-step reaction with 4 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

4: 93 percent / acetone / 12 h / 40 °C

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