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

Base Information

Chemical Name:2-chloroethyl 2-O-(2-deoxy-3,4,6-tri-O-acetyl-2-[3-(trifluoromethyl)benzamido]-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-β-D-glucopyranosiduronamide
CAS No.:499115-49-0
Molecular Formula:C₂₉H₃₅ClF₃N₅O₁₃
Molecular Weight:754.071
Hs Code.:

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

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

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

There total 6 articles about 2-chloroethyl 2-O-(2-deoxy-3,4,6-tri-O-acetyl-2-[3-(trifluoromethyl)benzamido]-β-D-glucopyranosyl)-3-azido-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: 83.0%

: 107-07-3
2-chloro-ethanol

: 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

: 499115-49-0
2-chloroethyl 2-O-(2-deoxy-3,4,6-tri-O-acetyl-2-[3-(trifluoromethyl)benzamido]-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-β-D-glucopyranosiduronamide

Guidance literature:: With boron trifluoride diethyl etherate; mercury(II) trifluoroacetate; for 4.5h;
DOI:10.1016/S0040-4020(02)00743-3

Reference yield:

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

: 499115-49-0
2-chloroethyl 2-O-(2-deoxy-3,4,6-tri-O-acetyl-2-[3-(trifluoromethyl)benzamido]-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-β-D-glucopyranosiduronamide

Guidance literature:: Multi-step reaction with 3 steps

1: 93 percent / HATU; DIPEA / dimethylformamide / 12 h / 20 °C

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

3: 83 percent / BF₃*Et₂O; Hg(TFA)2 / 4.5 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; In 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

: 499115-49-0
2-chloroethyl 2-O-(2-deoxy-3,4,6-tri-O-acetyl-2-[3-(trifluoromethyl)benzamido]-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-β-D-glucopyranosiduronamide

Guidance literature:: Multi-step reaction with 3 steps

1: 93 percent / HATU; DIPEA / dimethylformamide / 12 h / 20 °C

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

3: 83 percent / BF₃*Et₂O; Hg(TFA)2 / 4.5 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; In N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(02)00743-3