phenyl 2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)-4,5-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:phenyl 2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)-4,5-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
CAS No.:492440-45-6
Molecular Formula:C₃₉H₃₉NO₁₃S
Molecular Weight:761.804
Hs Code.:

Synonyms:phenyl 2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)-4,5-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

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Chemical Property of phenyl 2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)-4,5-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

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Technology Process of phenyl 2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)-4,5-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

There total 10 articles about phenyl 2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)-4,5-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 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: 64.0%

: 108-24-7
acetic anhydride

: 2-[(2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-8-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-isoindole-1,3-dione

: 492440-45-6
phenyl 2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)-4,5-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: With pyridine; dmap; Inert atmosphere;
DOI:10.1002/anie.201101055

Reference yield:

: 73-34-7,87-96-7,488-79-9,551-63-3,609-01-8,643-17-4,643-18-5,4164-09-4,6014-42-2,6155-36-8,6189-71-5,6696-41-9,6736-43-2,13224-93-6,22611-09-2,28161-49-1,28161-50-4,28161-52-6,45864-36-6,63814-64-2,71116-59-1,71116-61-5,72598-05-1,87936-88-7,87936-89-8,97466-79-0,116908-82-8,120442-60-6,123484-22-0,133576-32-6
6-deoxy-L-galactose

: 492440-45-6
phenyl 2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)-4,5-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 90 percent / Et₃N / dimethylformamide / 0 - 20 °C

2.1: Me₃SiI / CH₂Cl₂ / 0.33 h / 20 °C

2.2: 2,6-di-tert-butylpyridine / CH₂Cl₂ / 20 °C

2.3: MeOH / CH₂Cl₂ / 0.5 h / 20 °C

3.1: 0.32 g / pyridine / 20 °C

With pyridine; trimethylsilyl iodide; triethylamine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0957-4166(02)00480-9

Reference yield:

: 79528-49-7
phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 492440-45-6
phenyl 2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)-4,5-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: 100 percent / MeONa / methanol / 3 h / 20 °C

2.1: 86 percent / p-TsOH / acetonitrile / 2 h / 20 °C

3.1: Me₃SiI / CH₂Cl₂ / 0.33 h / 20 °C

3.2: 2,6-di-tert-butylpyridine / CH₂Cl₂ / 20 °C

3.3: MeOH / CH₂Cl₂ / 0.5 h / 20 °C

4.1: 0.32 g / pyridine / 20 °C

With pyridine; trimethylsilyl iodide; sodium methylate; toluene-4-sulfonic acid; In methanol; dichloromethane; acetonitrile;
DOI:10.1016/S0957-4166(02)00480-9