4-O-acetyl-3-acetamido-2-O-benzyl-3-deoxy-D-fucopyranosyl N-phenyl-trifuoroacetimidate

Base Information

Chemical Name:4-O-acetyl-3-acetamido-2-O-benzyl-3-deoxy-D-fucopyranosyl N-phenyl-trifuoroacetimidate
CAS No.:720694-52-0
Molecular Formula:C₂₅H₂₇F₃N₂O₆
Molecular Weight:508.494
Hs Code.:

Synonyms:4-O-acetyl-3-acetamido-2-O-benzyl-3-deoxy-D-fucopyranosyl N-phenyl-trifuoroacetimidate

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Chemical Property of 4-O-acetyl-3-acetamido-2-O-benzyl-3-deoxy-D-fucopyranosyl N-phenyl-trifuoroacetimidate

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Technology Process of 4-O-acetyl-3-acetamido-2-O-benzyl-3-deoxy-D-fucopyranosyl N-phenyl-trifuoroacetimidate

There total 6 articles about 4-O-acetyl-3-acetamido-2-O-benzyl-3-deoxy-D-fucopyranosyl N-phenyl-trifuoroacetimidate 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: 67.0%

: 61881-19-4
2,2,2-trifluoro-N-phenyl-acetimidoyl chloride

: 4-O-acetyl-3-acetamido-2-O-benzyl-3-deoxy-D-fucopyranose

: 720694-52-0
4-O-acetyl-3-acetamido-2-O-benzyl-3-deoxy-D-fucopyranosyl N-phenyl-trifuoroacetimidate

Guidance literature:: With sodium hydride; In dichloromethane; at 0 ℃;
DOI:10.1016/j.tetlet.2004.04.065

Reference yield:

: 201858-29-9
allyl α-D-isopropylidene-α-D-fucopyranoside

: 720694-52-0
4-O-acetyl-3-acetamido-2-O-benzyl-3-deoxy-D-fucopyranosyl N-phenyl-trifuoroacetimidate

Guidance literature:: Multi-step reaction with 9 steps

1.1: CSA / dimethylformamide / 40 °C

1.2: pyridine; dimethylformamide / 20 °C

1.3: 58 percent / AcOH / pyridine; dimethylformamide / 20 °C

2.1: CSA / CH₂Cl₂; pyridine / 0.67 h / 0 °C

3.1: NaOMe / methanol; CH₂Cl₂ / 2 h / 20 °C

4.1: DBU / CH₂Cl₂ / 1 h / 0 °C

5.1: 965 mg / silica gel (0.063-0.200 mm) / CHCl₃ / 0.17 h / 45 °C

6.1: 68 percent / NaH / dimethylformamide / 20 °C

7.1: aq. HCl / tetrahydrofuran / 20 °C

7.2: 63 percent / pyridine / 20 °C

8.1: 84 percent / PdCl₂ / methanol; CH₂Cl₂ / 20 °C

9.1: 67 percent / NaH; 4A MS / CH₂Cl₂ / 0 °C

With hydrogenchloride; camphor-10-sulfonic acid; sodium methylate; silica gel; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium dichloride; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2004.04.065

Reference yield:

: (1R,2S,4R,5S,6R)-2-Allyloxy-4-methyl-3,7-dioxa-bicyclo[4.1.0]heptan-5-ol

: 720694-52-0
4-O-acetyl-3-acetamido-2-O-benzyl-3-deoxy-D-fucopyranosyl N-phenyl-trifuoroacetimidate

Guidance literature:: Multi-step reaction with 6 steps

1.1: DBU / CH₂Cl₂ / 1 h / 0 °C

2.1: 965 mg / silica gel (0.063-0.200 mm) / CHCl₃ / 0.17 h / 45 °C

3.1: 68 percent / NaH / dimethylformamide / 20 °C

4.1: aq. HCl / tetrahydrofuran / 20 °C

4.2: 63 percent / pyridine / 20 °C

5.1: 84 percent / PdCl₂ / methanol; CH₂Cl₂ / 20 °C

6.1: 67 percent / NaH; 4A MS / CH₂Cl₂ / 0 °C

With hydrogenchloride; silica gel; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium dichloride; In tetrahydrofuran; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2004.04.065