Allyl 2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-5-O-allyl-3-O-phenoxycarbonyl-α-D-glucofuranosiduronamide

Base Information

Chemical Name:Allyl 2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-5-O-allyl-3-O-phenoxycarbonyl-α-D-glucofuranosiduronamide
CAS No.:220827-28-1
Molecular Formula:C₃₃H₃₉Cl₃N₂O₁₆
Molecular Weight:826.035
Hs Code.:

Synonyms:Allyl 2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-5-O-allyl-3-O-phenoxycarbonyl-α-D-glucofuranosiduronamide

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Chemical Property of Allyl 2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-5-O-allyl-3-O-phenoxycarbonyl-α-D-glucofuranosiduronamide

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Technology Process of Allyl 2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-5-O-allyl-3-O-phenoxycarbonyl-α-D-glucofuranosiduronamide

There total 6 articles about Allyl 2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-5-O-allyl-3-O-phenoxycarbonyl-α-D-glucofuranosiduronamide 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: 76.0%

: 161545-19-3
3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-α/β-D-glucopyranose trichloroacetimidate

: 220827-26-9
allyl 5-O-allyl-3-O-phenoxycarbonyl-α-D-glucofuranosiduronamide

: 220827-28-1
Allyl 2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-5-O-allyl-3-O-phenoxycarbonyl-α-D-glucofuranosiduronamide

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; In 1,2-dichloro-ethane; toluene; at 10 ℃; for 5h;
DOI:10.1016/S0040-4020(98)01063-1

Reference yield:

: 126214-82-2
1,2-O-isopropyliden-5-O-allyl-α-D-glucofuranosidurono-6,3-lactone

: 220827-28-1
Allyl 2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-5-O-allyl-3-O-phenoxycarbonyl-α-D-glucofuranosiduronamide

Guidance literature:: Multi-step reaction with 5 steps

1: NH₃ / methanol

2: 96 percent / DMAP / Et₃N / CH₂Cl₂ / 1 h / 20 °C

3: 95 percent / trifluoroacetic acid; water / 0.67 h / 20 °C

4: 25 percent / Dowex 50 W X₂ (H⁺ form); 3-Angstroem molecular sieves / 2.5 h / 20 °C

5: 76 percent / 3-Angstroem molecular sieves; trimethylsilyltriflate / 1,2-dichloro-ethane; toluene / 5 h / 10 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; Dowex 50 W X₂ (H⁺ form); ammonia; water; trifluoroacetic acid; triethylamine; In methanol; dichloromethane; 1,2-dichloro-ethane; toluene; 1: Ring cleavage / 2: Esterification / 3: Hydrolysis / 4: Alkylation / 5: Condensation;
DOI:10.1016/S0040-4020(98)01063-1

Reference yield:

: 156325-49-4
1,2-O-isopropyliden-5-O-allyl-α-D-glucofuranosiduronamide

: 220827-28-1
Allyl 2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-5-O-allyl-3-O-phenoxycarbonyl-α-D-glucofuranosiduronamide

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / DMAP / Et₃N / CH₂Cl₂ / 1 h / 20 °C

2: 95 percent / trifluoroacetic acid; water / 0.67 h / 20 °C

3: 25 percent / Dowex 50 W X₂ (H⁺ form); 3-Angstroem molecular sieves / 2.5 h / 20 °C

4: 76 percent / 3-Angstroem molecular sieves; trimethylsilyltriflate / 1,2-dichloro-ethane; toluene / 5 h / 10 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; Dowex 50 W X₂ (H⁺ form); water; trifluoroacetic acid; triethylamine; In dichloromethane; 1,2-dichloro-ethane; toluene; 1: Esterification / 2: Hydrolysis / 3: Alkylation / 4: Condensation;
DOI:10.1016/S0040-4020(98)01063-1