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

Base Information

Chemical Name:(2R,4R,6S)-2-Benzyloxymethyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-ol
CAS No.:247146-19-6
Molecular Formula:C₂₃H₄₀O₄Si
Molecular Weight:408.654
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 5 articles about (2R,4R,6S)-2-Benzyloxymethyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-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: 89.0%

: 247146-45-8
(2R,4S,6S)-2-Benzyloxymethyl-4-triethylsilanyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-ol

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

Guidance literature:: With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -20 ℃;
DOI:10.1021/ja990860j

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 steps

1: imidazole / CH₂Cl₂ / 0 °C

2: tetrahydrofuran / -78 - -50 °C

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

With 1H-imidazole; triethylsilane; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane; 1: silylation / 2: Addition / 3: Reduction;
DOI:10.1021/ja990860j

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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

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