methyl 6-O-acetyl-3-O-benzyl-β-D-fructofuranosyl-(2-1)-3,4,6-tri-O-benzyl-β-D-fructofuranoside

Base Information

• Chemical Name: methyl 6-O-acetyl-3-O-benzyl-β-D-fructofuranosyl-(2-1)-3,4,6-tri-O-benzyl-β-D-fructofuranoside
• CAS No.: 478810-22-9
• Molecular Formula: C₄₃H₅₀O₁₂
• Molecular Weight: 758.863

Synonyms:methyl 6-O-acetyl-3-O-benzyl-β-D-fructofuranosyl-(2-1)-3,4,6-tri-O-benzyl-β-D-fructofuranoside

Chemical Property of methyl 6-O-acetyl-3-O-benzyl-β-D-fructofuranosyl-(2-1)-3,4,6-tri-O-benzyl-β-D-fructofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of methyl 6-O-acetyl-3-O-benzyl-β-D-fructofuranosyl-(2-1)-3,4,6-tri-O-benzyl-β-D-fructofuranoside

There total 13 articles about methyl 6-O-acetyl-3-O-benzyl-β-D-fructofuranosyl-(2-1)-3,4,6-tri-O-benzyl-β-D-fructofuranoside 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: 93.0%

methyl 6-O-acetyl-3-O-benzyl-1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-fructofuranosyl-(2-1)-3,4,6-tri-O-benzyl-β-D-fructofuranoside (478810-21-8) → methyl 6-O-acetyl-3-O-benzyl-β-D-fructofuranosyl-(2-1)-3,4,6-tri-O-benzyl-β-D-fructofuranoside (478810-22-9)

Guidance literature:

With tris(dimethylamino)sulfonium trimethylsilyldifluoride; In N,N-dimethyl-formamide; for 1h;

DOI:10.1021/jo020341q

Reference yield:

D-fructose (470-23-5,470-24-6,10247-46-8,10489-79-9,35673-97-3,36441-90-4,36441-92-6,36468-68-5,37500-17-7,40461-86-7,40461-87-8,41579-20-8,41846-98-4,41846-99-5,41847-00-1,41847-01-2,41847-02-3,41847-03-4,41847-04-5,41847-05-6,41847-06-7,41847-51-2,41847-52-3,42744-42-3) → methyl 6-O-acetyl-3-O-benzyl-β-D-fructofuranosyl-(2-1)-3,4,6-tri-O-benzyl-β-D-fructofuranoside (478810-22-9)

Guidance literature:

Multi-step reaction with 8 steps

1: H₂SO₄

2: 55 percent / pyridine / 3 h / 20 °C

3: 60 percent / pyridine

4: TBAF / tetrahydrofuran / 1 h

5: NaH / dimethylformamide / 1 h

6: 47 mg / TFA; Et₃SiH / CH₂Cl₂ / 1 h

7: 86 percent / dimethyl(methylthio)sulfonium triflate; 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.67 h / 20 °C

8: 93 percent / tris(dimethylaminosulfonium) difluorotrimethylsilicate / dimethylformamide / 1 h

With pyridine; triethylsilane; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; sulfuric acid; tetrabutyl ammonium fluoride; tris(dimethylamino)sulfonium trimethylsilyldifluoride; sodium hydride; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo020341q

Reference yield:

methyl 6-O-(tert-butyldimethylsilyl)-β-D-fructofuranoside (147672-51-3) → methyl 6-O-acetyl-3-O-benzyl-β-D-fructofuranosyl-(2-1)-3,4,6-tri-O-benzyl-β-D-fructofuranoside (478810-22-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 60 percent / pyridine

2: TBAF / tetrahydrofuran / 1 h

3: NaH / dimethylformamide / 1 h

4: 47 mg / TFA; Et₃SiH / CH₂Cl₂ / 1 h

5: 86 percent / dimethyl(methylthio)sulfonium triflate; 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.67 h / 20 °C

6: 93 percent / tris(dimethylaminosulfonium) difluorotrimethylsilicate / dimethylformamide / 1 h

With pyridine; triethylsilane; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; tetrabutyl ammonium fluoride; tris(dimethylamino)sulfonium trimethylsilyldifluoride; sodium hydride; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo020341q

upstream raw materials:

methyl 6-O-acetyl-3-O-benzyl-1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-fructofuranosyl-(2-1)-3,4,6-tri-O-benzyl-β-D-fructofuranoside

D-fructose

methyl 6-O-(tert-butyldimethylsilyl)-β-D-fructofuranoside

methyl β-D-fructofuranoside

Downstream raw materials:

Acetic acid (2R,3R,4S,5R)-4-benzyloxy-5-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-2-methoxy-tetrahydro-furan-2-ylmethoxy)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

methyl 6-O-acetyl-4-O-benzoyl-3-O-benzyl-β-D-fructofuranosyl-(2-1)-3,4,6-tri-O-benzyl-β-D-fructofuranoside

methyl 3-O-benzyl-β-D-fructofuranosyl-(2-1)-3-O-benzyl-β-D-fructofuranosyl-(2-1)-3,4,6-tri-O-benzyl-β-D-fructofuranoside

methyl 6-O-acetyl-3-O-benzyl-1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-fructofuranosyl-(2-1)-6-O-acetyl-4-O-benzoyl-3-O-benzyl-β-D-fructofuranosyl-(2-1)-3,4,6-tri-O-benzyl-β-D-fructofuranoside

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