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

Base Information

Chemical Name:ethyl 6-O-acetyl-3-O-benzyl-1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-thio-β-D-fructofuranoside
CAS No.:478810-15-0
Molecular Formula:C₂₉H₅₀O₇SSi₂
Molecular Weight:598.949
Hs Code.:

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

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Chemical Property of ethyl 6-O-acetyl-3-O-benzyl-1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-thio-β-D-fructofuranoside

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Technology Process of ethyl 6-O-acetyl-3-O-benzyl-1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-thio-β-D-fructofuranoside

There total 4 articles about ethyl 6-O-acetyl-3-O-benzyl-1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-thio-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: 81.0%

: 69304-37-6
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

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

: 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

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at -30 - 20 ℃; for 6.5h;
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

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

Guidance literature:: Multi-step reaction with 4 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

With 1H-imidazole; 2,4,6-trimethyl-pyridine; triethylsilane; tetrabutyl ammonium fluoride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo020341q

Reference yield:

: 478810-12-7
ethyl 3-O-benzyl-1-O-(4,4'-dimethoxytriphenyl)methyl-2-thio-β-D-fructofuranoside

: 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

Guidance literature:: Multi-step reaction with 3 steps

1: 97 percent / 2,4,6-collidine / CH₂Cl₂ / 2 h / -70 °C

2: 86 percent / TFA; Et₃SiH / CH₂Cl₂ / 0.5 h

3: 81 percent / imidazole / dimethylformamide / 6.5 h / -30 - 20 °C

With 1H-imidazole; 2,4,6-trimethyl-pyridine; triethylsilane; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo020341q