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

Base Information

• Chemical Name: 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
• CAS No.: 212558-11-7
• Molecular Formula: C₂₉H₃₆O₁₅
• Molecular Weight: 624.596
• Mol file: 212558-11-7.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 1 articles about 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 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: 71.0%

2,3-di-O-acetyl-1,6-anhydro-β-D-glucose (22331-11-9) + 2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranosyl bromide (34339-69-0) → 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 (212558-11-7)

Guidance literature:

With silver trifluoromethanesulfonate; In dichloromethane; toluene; at -35 ℃; for 15h;

DOI:10.1080/07328309808002339

Reference yield:

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 (212558-11-7) → (2S,3S,4S,5R,6R)-3,5-Bis-benzoyloxy-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)-4-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:

Multi-step reaction with 7 steps

1: MeOH / methanol / 3 h

3: ZnI₂ / CH₂Cl₂

4: TFA / CH₂Cl₂; H₂O

5: 73.6 percent / pyridine / 0.5 h

6: 84 percent / 4 Angstroem MS, DMTST / CH₂Cl₂ / 0.5 h

7: 86 percent / H₂ / Pd/C / ethyl acetate / 4654.3 Torr

With methanol; 4 Angstroem MS; hydrogen; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; trifluoroacetic acid; zinc(II) iodide; palladium on activated charcoal; In pyridine; methanol; dichloromethane; water; ethyl acetate;

DOI:10.1080/07328309808002339

Reference yield:

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 (212558-11-7) → (2S,3S,4S,5R,6R)-3,5-Bis-benzoyloxy-4-benzyloxy-6-[(R)-methoxycarbonyl-((2R,4R)-2-methoxycarbonyl-[1,3]dioxolan-4-yl)-methoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: MeOH / methanol / 3 h

With methanol; In methanol;

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

Downstream raw materials:

(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

(2S,3S,4S,5R,6R)-3,5-Bis-benzoyloxy-4-benzyloxy-6-((2R,3R,4S,5R,6S)-4,5-bis-benzoyloxy-2-benzoyloxymethyl-6-cyclohexylsulfanyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

(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