(2S,3R,6S)-6-Hydroxymethyl-2-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-3,6-dihydro-2H-pyran-3-ol

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Chemical Name:(2S,3R,6S)-6-Hydroxymethyl-2-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-3,6-dihydro-2H-pyran-3-ol
CAS No.:175550-11-5
Molecular Formula:C₂₀H₃₀O₃SSi
Molecular Weight:378.608
Hs Code.:

Synonyms:(2S,3R,6S)-6-Hydroxymethyl-2-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-3,6-dihydro-2H-pyran-3-ol

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Chemical Property of (2S,3R,6S)-6-Hydroxymethyl-2-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-3,6-dihydro-2H-pyran-3-ol

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Technology Process of (2S,3R,6S)-6-Hydroxymethyl-2-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-3,6-dihydro-2H-pyran-3-ol

There total 7 articles about (2S,3R,6S)-6-Hydroxymethyl-2-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-3,6-dihydro-2H-pyran-3-ol 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%

: 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

: 175550-11-5
(2S,3R,6S)-6-Hydroxymethyl-2-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-3,6-dihydro-2H-pyran-3-ol

Guidance literature:: With sodium methylate; In methanol; at 0 ℃; for 0.75h;
DOI:10.1016/0040-4020(96)00008-7

Reference yield:

: 63139-23-1
phenylthioethynyl trimethylsilane

: 175550-11-5
(2S,3R,6S)-6-Hydroxymethyl-2-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-3,6-dihydro-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 6 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

6: 95 percent / sodium methoxide / methanol / 0.75 h / 0 °C

With 1H-imidazole; sodium hexachloroplatinate; sodium tetrahydroborate; cerium(III) chloride; dicobalt octacarbonyl; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; iodine; sodium methylate; sodium hydrogencarbonate; In tetrahydrofuran; methanol; 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

: 175550-11-5
(2S,3R,6S)-6-Hydroxymethyl-2-((Z)-2-phenylsulfanyl-2-triethylsilanyl-vinyl)-3,6-dihydro-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 5 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

5: 95 percent / sodium methoxide / methanol / 0.75 h / 0 °C

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