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

Base Information

Chemical Name: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
CAS No.:478810-24-1
Molecular Formula:C₇₇H₉₈O₂₀Si₂
Molecular Weight:1399.78
Hs Code.:

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

Synonyms: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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Chemical Property of 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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Technology Process of 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

There total 18 articles about 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 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%

: 478810-15-0
ethyl 6-O-acetyl-3-O-benzyl-1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-thio-β-D-fructofuranoside

: 478810-23-0
methyl 6-O-acetyl-4-O-benzoyl-3-O-benzyl-β-D-fructofuranosyl-(2-1)-3,4,6-tri-O-benzyl-β-D-fructofuranoside

: 478810-24-1
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

Guidance literature:: With 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In dichloromethane; at 20 ℃; for 0.666667h;
DOI:10.1021/jo020341q

Reference yield:

: 302905-20-0
ethyl 3-O-benzyl-6-O-tert-butyldimethylsilyl-1-O-(4,4'-dimethoxytriphenyl)methyl-2-thio-β-D-fructofuranoside

: 478810-24-1
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

Guidance literature:: Multi-step reaction with 10 steps

1: 90 percent / TBAF / tetrahydrofuran / 0.5 h

2: 97 percent / 2,4,6-collidine / CH₂Cl₂ / 2 h / -70 °C

3: 86 percent / TFA; Et₃SiH / CH₂Cl₂ / 0.5 h

4: 81 percent / imidazole / dimethylformamide / 6.5 h / -30 - 20 °C

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

7: pyridine; 4-DMAP / 60 °C

8: pyridine / CH₂Cl₂ / 3 h / 20 °C

9: 20 mg / TFA; Et₃SiH / CH₂Cl₂ / 0.33 h

10: 67 percent / dimethyl(methylthio)sulfonium triflate; 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.67 h / 20 °C

With pyridine; 1H-imidazole; 2,4,6-trimethyl-pyridine; triethylsilane; dmap; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; tetrabutyl ammonium fluoride; tris(dimethylamino)sulfonium trimethylsilyldifluoride; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo020341q

Reference yield:

: 478810-14-9
ethyl 6-O-acetyl-3-O-benzyl-2-thio-β-D-fructofuranoside

: 478810-24-1
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

Guidance literature:: Multi-step reaction with 7 steps

1: 81 percent / imidazole / dimethylformamide / 6.5 h / -30 - 20 °C

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

3: 93 percent / tris(dimethylaminosulfonium) difluorotrimethylsilicate / dimethylformamide / 1 h

4: pyridine; 4-DMAP / 60 °C

5: pyridine / CH₂Cl₂ / 3 h / 20 °C

6: 20 mg / TFA; Et₃SiH / CH₂Cl₂ / 0.33 h

7: 67 percent / dimethyl(methylthio)sulfonium triflate; 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.67 h / 20 °C

With pyridine; 1H-imidazole; triethylsilane; dmap; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; tris(dimethylamino)sulfonium trimethylsilyldifluoride; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo020341q