phenyl 2-O-(2-deoxy-3,4,6-tri-O-acetyl-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-3,4,6-tri-O-acetyl-2-[3-(trifluoromethyl)benzamido]-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide
CAS No.:394247-91-7
Molecular Formula:C₃₃H₃₆F₃N₅O₁₂S
Molecular Weight:783.736
Hs Code.:

phenyl 2-O-(2-deoxy-3,4,6-tri-O-acetyl-2-[3-(trifluoromethyl)benzamido]-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide

Synonyms:phenyl 2-O-(2-deoxy-3,4,6-tri-O-acetyl-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-3,4,6-tri-O-acetyl-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-3,4,6-tri-O-acetyl-2-[3-(trifluoromethyl)benzamido]-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide

There total 5 articles about phenyl 2-O-(2-deoxy-3,4,6-tri-O-acetyl-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: 92.0%

: 108-24-7
acetic anhydride

: 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

: 394247-91-7
phenyl 2-O-(2-deoxy-3,4,6-tri-O-acetyl-2-[3-(trifluoromethyl)benzamido]-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide

Guidance literature:: With pyridine; dmap; at 20 ℃; for 2h;
DOI:10.1016/S0040-4020(02)00743-3

Reference yield:

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

: 394247-91-7
phenyl 2-O-(2-deoxy-3,4,6-tri-O-acetyl-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: 93 percent / HATU; DIPEA / dimethylformamide / 12 h / 20 °C

2: 92 percent / DMAP; pyridine / 2 h / 20 °C

With pyridine; dmap; 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;
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

: 394247-91-7
phenyl 2-O-(2-deoxy-3,4,6-tri-O-acetyl-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: 74 percent / hydrazine / methanol; CH₂Cl₂ / 20 h / 20 °C

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

3: 92 percent / DMAP; pyridine / 2 h / 20 °C

With pyridine; dmap; 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:10.1016/S0040-4020(02)00743-3