(2S,3S,4S,5R,6R)-3,5-Bis-benzoyloxy-4-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzoyloxy-2-benzoyloxymethyl-6-{2-[4-(2,2,2-trifluoro-acetylamino)-phenyl]-ethoxy}-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,3S,4S,5R,6R)-3,5-Bis-benzoyloxy-4-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzoyloxy-2-benzoyloxymethyl-6-{2-[4-(2,2,2-trifluoro-acetylamino)-phenyl]-ethoxy}-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 212558-18-4
• Molecular Formula: C₆₅H₅₆F₃NO₁₈
• Molecular Weight: 1196.15

Synonyms:(2S,3S,4S,5R,6R)-3,5-Bis-benzoyloxy-4-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzoyloxy-2-benzoyloxymethyl-6-{2-[4-(2,2,2-trifluoro-acetylamino)-phenyl]-ethoxy}-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of (2S,3S,4S,5R,6R)-3,5-Bis-benzoyloxy-4-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzoyloxy-2-benzoyloxymethyl-6-{2-[4-(2,2,2-trifluoro-acetylamino)-phenyl]-ethoxy}-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

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Technology Process of (2S,3S,4S,5R,6R)-3,5-Bis-benzoyloxy-4-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzoyloxy-2-benzoyloxymethyl-6-{2-[4-(2,2,2-trifluoro-acetylamino)-phenyl]-ethoxy}-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 7 articles about (2S,3S,4S,5R,6R)-3,5-Bis-benzoyloxy-4-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzoyloxy-2-benzoyloxymethyl-6-{2-[4-(2,2,2-trifluoro-acetylamino)-phenyl]-ethoxy}-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 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:

2,3-di-O-acetyl-1,6-anhydro-β-D-glucose (22331-11-9) → (2S,3S,4S,5R,6R)-3,5-Bis-benzoyloxy-4-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzoyloxy-2-benzoyloxymethyl-6-{2-[4-(2,2,2-trifluoro-acetylamino)-phenyl]-ethoxy}-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (212558-18-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 71 percent / AgOTf / toluene; CH₂Cl₂ / 15 h / -35 °C

2: MeOH / methanol / 3 h

4: ZnI₂ / CH₂Cl₂

5: TFA / CH₂Cl₂; H₂O

6: 73.6 percent / pyridine / 0.5 h

7: 84 percent / 4 Angstroem MS, DMTST / CH₂Cl₂ / 0.5 h

With methanol; 4 Angstroem MS; silver trifluoromethanesulfonate; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; trifluoroacetic acid; zinc(II) iodide; In pyridine; methanol; dichloromethane; water; toluene;

DOI:10.1080/07328309808002339

Reference yield:

2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranosyl bromide (34339-69-0) → (2S,3S,4S,5R,6R)-3,5-Bis-benzoyloxy-4-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzoyloxy-2-benzoyloxymethyl-6-{2-[4-(2,2,2-trifluoro-acetylamino)-phenyl]-ethoxy}-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (212558-18-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 71 percent / AgOTf / toluene; CH₂Cl₂ / 15 h / -35 °C

2: MeOH / methanol / 3 h

4: ZnI₂ / CH₂Cl₂

5: TFA / CH₂Cl₂; H₂O

6: 73.6 percent / pyridine / 0.5 h

7: 84 percent / 4 Angstroem MS, DMTST / CH₂Cl₂ / 0.5 h

With methanol; 4 Angstroem MS; silver trifluoromethanesulfonate; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; trifluoroacetic acid; zinc(II) iodide; In pyridine; methanol; dichloromethane; water; toluene;

DOI:10.1080/07328309808002339

Reference yield:

(1R,2S,3R,4R,5R)-2-((2S,3R,4S,5R,6R)-4-Benzyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6,8-dioxa-bicyclo[3.2.1]octane-3,4-diol → (2S,3S,4S,5R,6R)-3,5-Bis-benzoyloxy-4-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5-bis-benzoyloxy-2-benzoyloxymethyl-6-{2-[4-(2,2,2-trifluoro-acetylamino)-phenyl]-ethoxy}-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (212558-18-4)

Guidance literature:

Multi-step reaction with 5 steps

2: ZnI₂ / CH₂Cl₂

3: TFA / CH₂Cl₂; H₂O

4: 73.6 percent / pyridine / 0.5 h

5: 84 percent / 4 Angstroem MS, DMTST / CH₂Cl₂ / 0.5 h

With 4 Angstroem MS; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; trifluoroacetic acid; zinc(II) iodide; In pyridine; dichloromethane; water;

DOI:10.1080/07328309808002339

upstream raw materials:

2,3-di-O-acetyl-1,6-anhydro-β-D-glucose

2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranosyl bromide

2,3-di-O-acetyl-1,6-anhydro-4-O-(2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl)-β-D-glucopyranose

(2S,3S,4S,5R,6R)-3,5-Bis-benzoyloxy-4-benzyloxy-6-((1R,2R,3S,4R,5R)-3,4-bis-benzoyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

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