2-chloroethyl 2-O-(2-deoxy-2-[3-(trifluoromethyl)benzamido]-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-3-[3-[4-chloro-3-(trifluoromethyl)phenyl]ureido]-3-deoxy-4-O-methyl-β-D-glucopyranosiduronamide

Base Information

Chemical Name:2-chloroethyl 2-O-(2-deoxy-2-[3-(trifluoromethyl)benzamido]-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-3-[3-[4-chloro-3-(trifluoromethyl)phenyl]ureido]-3-deoxy-4-O-methyl-β-D-glucopyranosiduronamide
CAS No.:612844-82-3
Molecular Formula:C₃₇H₄₀Cl₂F₆N₄O₁₄
Molecular Weight:949.639
Hs Code.:

2-chloroethyl 2-O-(2-deoxy-2-[3-(trifluoromethyl)benzamido]-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-3-[3-[4-chloro-3-(trifluoromethyl)phenyl]ureido]-3-deoxy-4-O-methyl-β-D-glucopyranosiduronamide

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Chemical Property of 2-chloroethyl 2-O-(2-deoxy-2-[3-(trifluoromethyl)benzamido]-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-3-[3-[4-chloro-3-(trifluoromethyl)phenyl]ureido]-3-deoxy-4-O-methyl-β-D-glucopyranosiduronamide

Chemical Property:

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Technology Process of 2-chloroethyl 2-O-(2-deoxy-2-[3-(trifluoromethyl)benzamido]-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-3-[3-[4-chloro-3-(trifluoromethyl)phenyl]ureido]-3-deoxy-4-O-methyl-β-D-glucopyranosiduronamide

There total 8 articles about 2-chloroethyl 2-O-(2-deoxy-2-[3-(trifluoromethyl)benzamido]-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-3-[3-[4-chloro-3-(trifluoromethyl)phenyl]ureido]-3-deoxy-4-O-methyl-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:

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

: 612844-82-3
2-chloroethyl 2-O-(2-deoxy-2-[3-(trifluoromethyl)benzamido]-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-3-[3-[4-chloro-3-(trifluoromethyl)phenyl]ureido]-3-deoxy-4-O-methyl-β-D-glucopyranosiduronamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: 93 percent / HATU; DIPEA / dimethylformamide / 12 h / 20 °C

2.1: 92 percent / DMAP; pyridine / 2 h / 20 °C

3.1: 83 percent / BF₃*Et₂O; Hg(TFA)2 / 4.5 h

4.1: P(CH₃)3 / tetrahydrofuran; ethanol / 1.5 h

4.2: H₂O / tetrahydrofuran; ethanol / 12 h

5.1: 72 mg / CH₂Cl₂; dimethylformamide / 3.5 h

With pyridine; dmap; boron trifluoride diethyl etherate; mercury(II) trifluoroacetate; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; trimethylphosphane; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(02)00743-3

Reference yield:

: 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

: 612844-82-3
2-chloroethyl 2-O-(2-deoxy-2-[3-(trifluoromethyl)benzamido]-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-3-[3-[4-chloro-3-(trifluoromethyl)phenyl]ureido]-3-deoxy-4-O-methyl-β-D-glucopyranosiduronamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: 83 percent / BF₃*Et₂O; Hg(TFA)2 / 4.5 h

2.1: P(CH₃)3 / tetrahydrofuran; ethanol / 1.5 h

2.2: H₂O / tetrahydrofuran; ethanol / 12 h

3.1: 72 mg / CH₂Cl₂; dimethylformamide / 3.5 h

With boron trifluoride diethyl etherate; mercury(II) trifluoroacetate; trimethylphosphane; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(02)00743-3

Reference yield:

: 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

: 612844-82-3
2-chloroethyl 2-O-(2-deoxy-2-[3-(trifluoromethyl)benzamido]-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-3-[3-[4-chloro-3-(trifluoromethyl)phenyl]ureido]-3-deoxy-4-O-methyl-β-D-glucopyranosiduronamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: 93 percent / HATU; DIPEA / dimethylformamide / 12 h / 20 °C

2.1: 92 percent / DMAP; pyridine / 2 h / 20 °C

3.1: 83 percent / BF₃*Et₂O; Hg(TFA)2 / 4.5 h

4.1: P(CH₃)3 / tetrahydrofuran; ethanol / 1.5 h

4.2: H₂O / tetrahydrofuran; ethanol / 12 h

5.1: 72 mg / CH₂Cl₂; dimethylformamide / 3.5 h

With pyridine; dmap; boron trifluoride diethyl etherate; mercury(II) trifluoroacetate; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; trimethylphosphane; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(02)00743-3