(2R,3S,4R,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxytetrahydro-2H-pyran-3-ol

Base Information

Chemical Name:(2R,3S,4R,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxytetrahydro-2H-pyran-3-ol
CAS No.:925683-96-1
Molecular Formula:C₂₀H₃₄O₅Si
Molecular Weight:382.572
Hs Code.:

Synonyms:(2R,3S,4R,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxytetrahydro-2H-pyran-3-ol

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Chemical Property of (2R,3S,4R,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxytetrahydro-2H-pyran-3-ol

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Technology Process of (2R,3S,4R,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxytetrahydro-2H-pyran-3-ol

There total 5 articles about (2R,3S,4R,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxytetrahydro-2H-pyran-3-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: 71.0%

: 122795-03-3
methyl 2-deoxy-6-O-TBDMS-α-D-glucopyranoside

: 100-44-7
benzyl chloride

: 925683-96-1
(2R,3S,4R,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxytetrahydro-2H-pyran-3-ol

Guidance literature:: With dibutyltin chloride; tetrabutylammomium bromide; potassium carbonate; In acetonitrile; at 80 ℃; for 24h; regioselective reaction;
DOI:10.1016/j.tetlet.2017.08.043

Reference yield:

: 6752-48-3
(4aR,6S,8R,8aS)-6-methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-ol

: 925683-96-1
(2R,3S,4R,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxytetrahydro-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 78 percent / NaH; TBAI / tetrahydrofuran / 4 h / Heating

2: 79 percent / PTSA / methanol / 12 h

3: 83 percent / imidazole / CH₂Cl₂ / 4 h / 20 °C

With 1H-imidazole; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1055/s-2006-950325

Reference yield:

: 6087-40-7
(2R,3S,4R,6S)-3,4-diacetoxy-2-(acetoxymethyl)-6-methoxytetrahydro-2H-pyran

: 925683-96-1
(2R,3S,4R,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxytetrahydro-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1: NaOMe / methanol / 1 h / 20 °C

2: 7.4 g / PTSA / toluene / 6 h / Heating

3: 78 percent / NaH; TBAI / tetrahydrofuran / 4 h / Heating

4: 79 percent / PTSA / methanol / 12 h

5: 83 percent / imidazole / CH₂Cl₂ / 4 h / 20 °C

With 1H-imidazole; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1055/s-2006-950325