trimethyl [5S,6S,7S]-7-(t-butyldiphenylsilyloxy)-5,6-isopropylidenedioxy-4-oxo-7-phenyl-3-phenylsulfonylorthoheptanoate

Base Information

Chemical Name:trimethyl [5S,6S,7S]-7-(t-butyldiphenylsilyloxy)-5,6-isopropylidenedioxy-4-oxo-7-phenyl-3-phenylsulfonylorthoheptanoate
CAS No.:252273-58-8
Molecular Formula:C₄₁H₅₀O₉SSi
Molecular Weight:746.994
Hs Code.:

Synonyms:trimethyl [5S,6S,7S]-7-(t-butyldiphenylsilyloxy)-5,6-isopropylidenedioxy-4-oxo-7-phenyl-3-phenylsulfonylorthoheptanoate

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Chemical Property of trimethyl [5S,6S,7S]-7-(t-butyldiphenylsilyloxy)-5,6-isopropylidenedioxy-4-oxo-7-phenyl-3-phenylsulfonylorthoheptanoate

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Technology Process of trimethyl [5S,6S,7S]-7-(t-butyldiphenylsilyloxy)-5,6-isopropylidenedioxy-4-oxo-7-phenyl-3-phenylsulfonylorthoheptanoate

There total 8 articles about trimethyl [5S,6S,7S]-7-(t-butyldiphenylsilyloxy)-5,6-isopropylidenedioxy-4-oxo-7-phenyl-3-phenylsulfonylorthoheptanoate 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: 95.0%

: 38435-08-4
trimethyl 3-(phenylsulfonyl)orthopropionate

: 252273-57-7
ethyl (2S,3R,4S)-4-(t-butyldiphenylsilyloxy)-2,3-isopropylidenedioxy-4-phenylbutanoate

: 252273-58-8
trimethyl [5S,6S,7S]-7-(t-butyldiphenylsilyloxy)-5,6-isopropylidenedioxy-4-oxo-7-phenyl-3-phenylsulfonylorthoheptanoate

Guidance literature:: With n-butyllithium; In tetrahydrofuran; from -78 deg C to room temp.;
DOI:10.1016/S0040-4039(96)02439-2

Reference yield:

: 187931-99-3
ethyl (4S,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate

: 252273-58-8
trimethyl [5S,6S,7S]-7-(t-butyldiphenylsilyloxy)-5,6-isopropylidenedioxy-4-oxo-7-phenyl-3-phenylsulfonylorthoheptanoate

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / Et₃N*3HF / acetonitrile / 168 h / 20 °C

2: 97 percent / Ph₃P; ethyl azodicarboxylate / tetrahydrofuran / 1.75 h / 0 - 20 °C

3: 87 percent / K₂CO₃ / CH₂Cl₂; ethanol / 1 h / 20 °C

4: 94 percent / imidazole / dimethylformamide / 96 h / 20 °C

5: 90 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / -78 - 20 °C

With 1H-imidazole; n-butyllithium; ethyl azodicarboxylate; potassium carbonate; triethylamine tris(hydrogen fluoride); triphenylphosphine; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: desilylation / 2: Mitsunobu reaction / 3: saponification / 4: silylation / 5: Julia coupling;
DOI:10.1016/S0040-4020(99)00794-2

Reference yield:

: 252273-55-5
ethyl (2S,3R,4S)-2,3-isopropylidenedioxy-4-(4-nitrobenzyloxy)-4-phenylbutanoate

: 252273-58-8
trimethyl [5S,6S,7S]-7-(t-butyldiphenylsilyloxy)-5,6-isopropylidenedioxy-4-oxo-7-phenyl-3-phenylsulfonylorthoheptanoate

Guidance literature:: Multi-step reaction with 3 steps

1: 87 percent / K₂CO₃ / CH₂Cl₂; ethanol / 1 h / 20 °C

2: 94 percent / imidazole / dimethylformamide / 96 h / 20 °C

3: 90 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / -78 - 20 °C

With 1H-imidazole; n-butyllithium; potassium carbonate; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; 1: saponification / 2: silylation / 3: Julia coupling;
DOI:10.1016/S0040-4020(99)00794-2