Acetic acid (2S,5R,6R)-5-(tert-butyl-diphenyl-silanyloxy)-6-phenylsulfanylethynyl-5,6-dihydro-2H-pyran-2-ylmethyl ester

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Chemical Name:Acetic acid (2S,5R,6R)-5-(tert-butyl-diphenyl-silanyloxy)-6-phenylsulfanylethynyl-5,6-dihydro-2H-pyran-2-ylmethyl ester
CAS No.:167107-99-5
Molecular Formula:C₃₂H₃₄O₄SSi
Molecular Weight:542.771
Hs Code.:

Synonyms:Acetic acid (2S,5R,6R)-5-(tert-butyl-diphenyl-silanyloxy)-6-phenylsulfanylethynyl-5,6-dihydro-2H-pyran-2-ylmethyl ester

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Chemical Property of Acetic acid (2S,5R,6R)-5-(tert-butyl-diphenyl-silanyloxy)-6-phenylsulfanylethynyl-5,6-dihydro-2H-pyran-2-ylmethyl ester

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Technology Process of Acetic acid (2S,5R,6R)-5-(tert-butyl-diphenyl-silanyloxy)-6-phenylsulfanylethynyl-5,6-dihydro-2H-pyran-2-ylmethyl ester

There total 2 articles about Acetic acid (2S,5R,6R)-5-(tert-butyl-diphenyl-silanyloxy)-6-phenylsulfanylethynyl-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: 98.0%

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

: 58479-61-1
tert-butylchlorodiphenylsilane

: 167107-99-5
Acetic acid (2S,5R,6R)-5-(tert-butyl-diphenyl-silanyloxy)-6-phenylsulfanylethynyl-5,6-dihydro-2H-pyran-2-ylmethyl ester

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 12h; Ambient temperature;
DOI:10.1016/0040-4020(96)00008-7

Reference yield:

: 3366-47-0
2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabinohex-1-enopyranose

: 167107-99-5
Acetic acid (2S,5R,6R)-5-(tert-butyl-diphenyl-silanyloxy)-6-phenylsulfanylethynyl-5,6-dihydro-2H-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 2 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

With 1H-imidazole; sodium tetrahydroborate; cerium(III) chloride; trimethylsilyl trifluoromethanesulfonate; In N,N-dimethyl-formamide;
DOI:10.1016/0040-4020(96)00008-7

Reference yield:

: 167107-99-5
Acetic acid (2S,5R,6R)-5-(tert-butyl-diphenyl-silanyloxy)-6-phenylsulfanylethynyl-5,6-dihydro-2H-pyran-2-ylmethyl ester

: (2S,3R,6S)-2-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-6-(tert-butyl-diphenyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 7 steps

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

2: 87 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.5 h / pH 6

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

4: 95 percent / sodium methoxide / methanol / 0.75 h / 0 °C

5: 94 percent / imidazole / dimethylformamide / 13 h / Ambient temperature

6: 90 percent / sodium hydrogen phosphate, m-chloroperbenzoic acid / CH₂Cl₂ / 0.33 h / 0 °C

7: 2.) potassium fluoride / 1.) THF, 25 deg C, 20 h, 2.) MeOH, overnight

With 1H-imidazole; sodium hexachloroplatinate; potassium fluoride; disodium hydrogenphosphate; dicobalt octacarbonyl; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; iodine; sodium methylate; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1016/0040-4020(96)00008-7