(3RS,6R)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-3-(phenylselenyl)-3,4,5,6-tetrahydro-2H-pyran-2-one

Base Information

Chemical Name:(3RS,6R)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-3-(phenylselenyl)-3,4,5,6-tetrahydro-2H-pyran-2-one
CAS No.:187851-98-5
Molecular Formula:C₂₈H₃₂O₃SeSi
Molecular Weight:523.606
Hs Code.:

Synonyms:(3RS,6R)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-3-(phenylselenyl)-3,4,5,6-tetrahydro-2H-pyran-2-one

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Chemical Property of (3RS,6R)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-3-(phenylselenyl)-3,4,5,6-tetrahydro-2H-pyran-2-one

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Technology Process of (3RS,6R)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-3-(phenylselenyl)-3,4,5,6-tetrahydro-2H-pyran-2-one

There total 5 articles about (3RS,6R)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-3-(phenylselenyl)-3,4,5,6-tetrahydro-2H-pyran-2-one 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: 50.0%

: 34837-55-3
Phenylselenyl bromide

: 175398-33-1
(R)-6-<<(tert-butyldiphenylsilyl)oxy>methyl>-3,4,5,6-tetrahydro-2H-pyran-2-one

: 187851-98-5
(3RS,6R)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-3-(phenylselenyl)-3,4,5,6-tetrahydro-2H-pyran-2-one

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 5h;
DOI:10.1021/jo962166h

Reference yield:

: 1577-22-6
5-hexenoic acid

: 187851-98-5
(3RS,6R)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-3-(phenylselenyl)-3,4,5,6-tetrahydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 89 percent / NaHCO₃ / dimethylformamide / 72 h / 45 °C

2: 51 percent / K₃Fe(CN)6, K₂CO₃, NaHCO₃, (DHQD)2-AQN, K₂OsO₂(OH)2 / 2-methyl-propan-2-ol / 48 h / 0 °C

3: 89 percent / imidazole / dimethylformamide / 15 h / 25 °C

4: 75 percent / anisole, CF₃CO₂H / 0.5 h / 25 °C

5: 50 percent / LDA / tetrahydrofuran / 5 h / -78 °C

With 1H-imidazole; (DHQD)2AQN; K₂OsO₂(OH)2; sodium hydrogencarbonate; potassium carbonate; methoxybenzene; trifluoroacetic acid; potassium hexacyanoferrate(III); lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jo962166h

Reference yield:

: 187851-95-2
(4-methoxyphenyl)methyl hex-5-enoate

: 187851-98-5
(3RS,6R)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-3-(phenylselenyl)-3,4,5,6-tetrahydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 51 percent / K₃Fe(CN)6, K₂CO₃, NaHCO₃, (DHQD)2-AQN, K₂OsO₂(OH)2 / 2-methyl-propan-2-ol / 48 h / 0 °C

2: 89 percent / imidazole / dimethylformamide / 15 h / 25 °C

3: 75 percent / anisole, CF₃CO₂H / 0.5 h / 25 °C

4: 50 percent / LDA / tetrahydrofuran / 5 h / -78 °C

With 1H-imidazole; (DHQD)2AQN; K₂OsO₂(OH)2; sodium hydrogencarbonate; potassium carbonate; methoxybenzene; trifluoroacetic acid; potassium hexacyanoferrate(III); lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jo962166h