(2S,5S)-2-[(tert-butyldiphenylsilyl)oxymethyl]-5-[(1'R)-(1'-hydroxy)decyl]tetrahydrofuran

Base Information

Chemical Name:(2S,5S)-2-[(tert-butyldiphenylsilyl)oxymethyl]-5-[(1'R)-(1'-hydroxy)decyl]tetrahydrofuran
CAS No.:292069-16-0
Molecular Formula:C₃₂H₅₀O₃Si
Molecular Weight:510.833
Hs Code.:

Synonyms:(2S,5S)-2-[(tert-butyldiphenylsilyl)oxymethyl]-5-[(1'R)-(1'-hydroxy)decyl]tetrahydrofuran

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Chemical Property of (2S,5S)-2-[(tert-butyldiphenylsilyl)oxymethyl]-5-[(1'R)-(1'-hydroxy)decyl]tetrahydrofuran

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Technology Process of (2S,5S)-2-[(tert-butyldiphenylsilyl)oxymethyl]-5-[(1'R)-(1'-hydroxy)decyl]tetrahydrofuran

There total 13 articles about (2S,5S)-2-[(tert-butyldiphenylsilyl)oxymethyl]-5-[(1'R)-(1'-hydroxy)decyl]tetrahydrofuran 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: 37.0%

: 17049-50-2
n-decyl magnesium bromide

: 149099-14-9
(2S,5S)-5-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2-carboxaldehyde

: 292069-16-0
(2S,5S)-2-[(tert-butyldiphenylsilyl)oxymethyl]-5-[(1'R)-(1'-hydroxy)decyl]tetrahydrofuran

: 292069-18-2
(2S,5S)-2-[(tert-butyldiphenylsilyl)oxymethyl]-5-[(1'S)-(1'-hydroxy)decyl]tetrahydrofuran

Guidance literature:: With cerium(III) chloride; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃; for 20h;

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 292069-16-0
(2S,5S)-2-[(tert-butyldiphenylsilyl)oxymethyl]-5-[(1'R)-(1'-hydroxy)decyl]tetrahydrofuran

Guidance literature:: Multi-step reaction with 4 steps

1: 46 percent / imidazole / acetonitrile; tetrahydrofuran / 1 h / -78 °C

2: 96 percent / hydrogen / Pd/C / ethyl acetate / 24 h / 20 °C

3: 94 percent / oxalyl chloride; DMSO / CH₂Cl₂ / 1 h / -78 °C

4: 24 percent / CeCl₃ / tetrahydrofuran; diethyl ether / 20 h / -78 - 20 °C

With 1H-imidazole; cerium(III) chloride; oxalyl dichloride; hydrogen; dimethyl sulfoxide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; acetonitrile; 1: Etherification / 2: Catalytic hydrogenation / 3: Oxidation / 4: Alkylation;

Reference yield:

: 41107-82-8
2,5-anhydro-D-mannitol

: 292069-16-0
(2S,5S)-2-[(tert-butyldiphenylsilyl)oxymethyl]-5-[(1'R)-(1'-hydroxy)decyl]tetrahydrofuran

Guidance literature:: Multi-step reaction with 8 steps

1: 93 percent / pyridine / 7 h / 20 °C

2: 39 percent / pyridine / 13 h / 0 - 20 °C

3: 84 percent / zinc powder; NaI / dimethylformamide / 19 h / 140 °C

4: 92 percent / acetic acid; H₂O / 2 h / 50 °C

5: 46 percent / imidazole / acetonitrile; tetrahydrofuran / 1 h / -78 °C

6: 96 percent / hydrogen / Pd/C / ethyl acetate / 24 h / 20 °C

7: 94 percent / oxalyl chloride; DMSO / CH₂Cl₂ / 1 h / -78 °C

8: 24 percent / CeCl₃ / tetrahydrofuran; diethyl ether / 20 h / -78 - 20 °C

With pyridine; 1H-imidazole; cerium(III) chloride; oxalyl dichloride; hydrogen; dimethyl sulfoxide; sodium iodide; zinc; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1: Etherification / 2: Etherification / 3: Reduction / 4: deetherification / 5: Etherification / 6: Catalytic hydrogenation / 7: Oxidation / 8: Alkylation;