(2R,3S)-2-((R)-2-benzyloxypenta-3,4-dien-1-yl)tetrahydro-2H-pyran-3-ol

Base Information

Chemical Name:(2R,3S)-2-((R)-2-benzyloxypenta-3,4-dien-1-yl)tetrahydro-2H-pyran-3-ol
CAS No.:1456888-94-0
Molecular Formula:C₁₇H₂₂O₃
Molecular Weight:274.36
Hs Code.:

Synonyms:(2R,3S)-2-((R)-2-benzyloxypenta-3,4-dien-1-yl)tetrahydro-2H-pyran-3-ol

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Chemical Property of (2R,3S)-2-((R)-2-benzyloxypenta-3,4-dien-1-yl)tetrahydro-2H-pyran-3-ol

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Technology Process of (2R,3S)-2-((R)-2-benzyloxypenta-3,4-dien-1-yl)tetrahydro-2H-pyran-3-ol

There total 4 articles about (2R,3S)-2-((R)-2-benzyloxypenta-3,4-dien-1-yl)tetrahydro-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: 92.0%

: 1456888-95-1
C₂₃H₃₆O₃Si

: 1456888-94-0
(2R,3S)-2-((R)-2-benzyloxypenta-3,4-dien-1-yl)tetrahydro-2H-pyran-3-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1.5h; Inert atmosphere;
DOI:10.1016/j.tet.2013.08.026

Reference yield:

: 1456888-88-2
(R)-1-((2R,3S)-3-((tert-butyldimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)-3-(trimethylsilyl)penta-3,4-dien-2-ol

: 1456888-94-0
(2R,3S)-2-((R)-2-benzyloxypenta-3,4-dien-1-yl)tetrahydro-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium methylate / tetrahydrofuran / 7 h / 0 °C / Inert atmosphere

2.1: methanol; pyridinium p-toluenesulfonate / 0.5 h / 20 °C / Inert atmosphere

2.2: Inert atmosphere

3.1: tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane / tetrahydrofuran; toluene / 1 h / -10 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere

With methanol; tetrabutyl ammonium fluoride; sodium methylate; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; In tetrahydrofuran; toluene;
DOI:10.1016/j.tet.2013.08.026

Reference yield:

: C₂₂H₄₆O₃Si₃

: 1456888-94-0
(2R,3S)-2-((R)-2-benzyloxypenta-3,4-dien-1-yl)tetrahydro-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: methanol; pyridinium p-toluenesulfonate / 0.67 h / 20 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: sodium methylate / tetrahydrofuran / 7 h / 0 °C / Inert atmosphere

3.1: methanol; pyridinium p-toluenesulfonate / 0.5 h / 20 °C / Inert atmosphere

3.2: Inert atmosphere

4.1: tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane / tetrahydrofuran; toluene / 1 h / -10 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere

With methanol; tetrabutyl ammonium fluoride; sodium methylate; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; In tetrahydrofuran; toluene;
DOI:10.1016/j.tet.2013.08.026