(2R,6S)-2-Benzyloxymethyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-one

Base Information

Chemical Name:(2R,6S)-2-Benzyloxymethyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-one
CAS No.:247146-21-0
Molecular Formula:C₂₃H₃₈O₄Si
Molecular Weight:406.638
Hs Code.:

Synonyms:(2R,6S)-2-Benzyloxymethyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-one

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Chemical Property of (2R,6S)-2-Benzyloxymethyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-one

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Technology Process of (2R,6S)-2-Benzyloxymethyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-one

There total 5 articles about (2R,6S)-2-Benzyloxymethyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-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: 86.0%

: 247146-19-6
(2R,4R,6S)-2-Benzyloxymethyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-ol

: 247146-21-0
(2R,6S)-2-Benzyloxymethyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-one

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; at -78 ℃;
DOI:10.1021/ja990860j

Reference yield:

: (S)-4-Hydroxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-one

: 247146-21-0
(2R,6S)-2-Benzyloxymethyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-one

Guidance literature:: Multi-step reaction with 4 steps

1: imidazole / CH₂Cl₂ / 0 °C

2: tetrahydrofuran / -78 - -50 °C

3: 89 percent / BF₃*Et₂O; Et₃SiH / CH₂Cl₂ / -20 °C

4: 86 percent / (COCl)2; DMSO; Et₃N / -78 °C

With 1H-imidazole; triethylsilane; oxalyl dichloride; boron trifluoride diethyl etherate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1: silylation / 2: Addition / 3: Reduction / 4: Oxidation;
DOI:10.1021/ja990860j

Reference yield:

: (S)-5-Hydroxy-3-oxo-6-triisopropylsilanyloxy-hexanoic acid methyl ester

: 247146-21-0
(2R,6S)-2-Benzyloxymethyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-one

Guidance literature:: Multi-step reaction with 6 steps

1: Me₄NHB(OAc)3; AcOH / acetonitrile / -35 °C

2: PPTS / benzene / 80 °C

3: imidazole / CH₂Cl₂ / 0 °C

4: tetrahydrofuran / -78 - -50 °C

5: 89 percent / BF₃*Et₂O; Et₃SiH / CH₂Cl₂ / -20 °C

6: 86 percent / (COCl)2; DMSO; Et₃N / -78 °C

With 1H-imidazole; triethylsilane; oxalyl dichloride; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; acetic acid; dimethyl sulfoxide; triethylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; dichloromethane; acetonitrile; benzene; 1: Reduction / 2: lactonization / 3: silylation / 4: Addition / 5: Reduction / 6: Oxidation;
DOI:10.1021/ja990860j