Acetic acid (2S,5R,6S)-5-hydroxy-6-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-5,6-dihydro-2H-pyran-2-ylmethyl ester

Base Information

Chemical Name:Acetic acid (2S,5R,6S)-5-hydroxy-6-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-5,6-dihydro-2H-pyran-2-ylmethyl ester
CAS No.:175673-12-8
Molecular Formula:C₂₂H₃₂O₄SSi
Molecular Weight:420.645
Hs Code.:

Synonyms:Acetic acid (2S,5R,6S)-5-hydroxy-6-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-5,6-dihydro-2H-pyran-2-ylmethyl ester

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Chemical Property of Acetic acid (2S,5R,6S)-5-hydroxy-6-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-5,6-dihydro-2H-pyran-2-ylmethyl ester

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Technology Process of Acetic acid (2S,5R,6S)-5-hydroxy-6-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-5,6-dihydro-2H-pyran-2-ylmethyl ester

There total 6 articles about Acetic acid (2S,5R,6S)-5-hydroxy-6-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-5,6-dihydro-2H-pyran-2-ylmethyl ester 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%

: 617-86-7
triethylsilane

: 175673-11-7
Acetic acid (2S,5R,6S)-5-hydroxy-6-phenylsulfanylethynyl-5,6-dihydro-2H-pyran-2-ylmethyl ester

: 175673-12-8
Acetic acid (2S,5R,6S)-5-hydroxy-6-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-5,6-dihydro-2H-pyran-2-ylmethyl ester

Guidance literature:: With sodium hexachloroplatinate; sodium hydrogencarbonate; In diethyl ether; isopropyl alcohol; at 90 ℃; for 3h;
DOI:10.1016/0040-4020(96)00008-7

Reference yield:

: 63139-23-1
phenylthioethynyl trimethylsilane

: 175673-12-8
Acetic acid (2S,5R,6S)-5-hydroxy-6-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-5,6-dihydro-2H-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) trimethylsilyl trifluoromethanesulfonate, 2.) cerium(III) chloride, sodium borohydride / 1.) dichloromethane, 0 deg C, 12 h, 2.) methanol, 0 deg C, 3.5 h

2: 98 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

3: 1.) dicobaltoctacarbonyl, 2.) trifluoromethanesulfonic acid, 3.) iodine

4: 87 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.5 h / pH 6

5: 71 percent / sodium hydrogen carbonate, sodium hexachloroplatinate(IV) hexahydrate / diethyl ether; propan-2-ol / 3 h / 90 °C

With 1H-imidazole; sodium hexachloroplatinate; sodium tetrahydroborate; cerium(III) chloride; dicobalt octacarbonyl; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; iodine; sodium hydrogencarbonate; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1016/0040-4020(96)00008-7

Reference yield:

: 175550-09-1
Acetic acid (2S,5R,6R)-5-hydroxy-6-phenylsulfanylethynyl-5,6-dihydro-2H-pyran-2-ylmethyl ester

: 175673-12-8
Acetic acid (2S,5R,6S)-5-hydroxy-6-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-5,6-dihydro-2H-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

2: 1.) dicobaltoctacarbonyl, 2.) trifluoromethanesulfonic acid, 3.) iodine

3: 87 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.5 h / pH 6

4: 71 percent / sodium hydrogen carbonate, sodium hexachloroplatinate(IV) hexahydrate / diethyl ether; propan-2-ol / 3 h / 90 °C

With 1H-imidazole; sodium hexachloroplatinate; dicobalt octacarbonyl; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; iodine; sodium hydrogencarbonate; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1016/0040-4020(96)00008-7