phenyl 2-O-(2-deoxy-2-[3-(trifluoromethyl)benzamido]-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide

Base Information

Chemical Name:phenyl 2-O-(2-deoxy-2-[3-(trifluoromethyl)benzamido]-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide
CAS No.:612844-79-8
Molecular Formula:C₂₇H₃₀F₃N₅O₉S
Molecular Weight:657.625
Hs Code.:

Synonyms:phenyl 2-O-(2-deoxy-2-[3-(trifluoromethyl)benzamido]-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide

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Chemical Property of phenyl 2-O-(2-deoxy-2-[3-(trifluoromethyl)benzamido]-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide

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Technology Process of phenyl 2-O-(2-deoxy-2-[3-(trifluoromethyl)benzamido]-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide

There total 3 articles about phenyl 2-O-(2-deoxy-2-[3-(trifluoromethyl)benzamido]-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide 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%

: 454-92-2
3-(trifluoromethyl)benzoic acid

: 612844-78-7
phenyl 2-O-(2-amino-2-deoxy-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide

: 612844-79-8
phenyl 2-O-(2-deoxy-2-[3-(trifluoromethyl)benzamido]-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide

Guidance literature:: With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 12h;
DOI:10.1021/ja0166693 DOI:10.1016/S0040-4020(02)00743-3

Reference yield:

: phenyl 2-O-(2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronic acid

: 612844-79-8
phenyl 2-O-(2-deoxy-2-[3-(trifluoromethyl)benzamido]-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide

Guidance literature:: Multi-step reaction with 3 steps

1: 76 percent / pyridine; di-tert-butyl dicarbonate; NH₄HCO₃ / acetonitrile / 10 h / 20 °C

2: 74 percent / hydrazine / methanol; CH₂Cl₂ / 20 h / 20 °C

3: 93 percent / HATU; DIPEA / dimethylformamide / 12 h / 20 °C

With pyridine; di-tert-butyl dicarbonate; ammonium bicarbonate; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; hydrazine; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4020(02)00743-3

Reference yield:

: 302352-19-8
phenyl 2-O-(2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide

: 612844-79-8
phenyl 2-O-(2-deoxy-2-[3-(trifluoromethyl)benzamido]-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide

Guidance literature:: Multi-step reaction with 2 steps

1: 74 percent / hydrazine / methanol; CH₂Cl₂ / 20 h / 20 °C

2: 93 percent / HATU; DIPEA / dimethylformamide / 12 h / 20 °C

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; hydrazine; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja0166693 DOI:10.1016/S0040-4020(02)00743-3