(E)-3-((2R,3S,4R)-3,4-Bis-benzyloxy-3,4-dihydro-2H-pyran-2-yl)-acrylic acid tert-butyl ester

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Chemical Name:(E)-3-((2R,3S,4R)-3,4-Bis-benzyloxy-3,4-dihydro-2H-pyran-2-yl)-acrylic acid tert-butyl ester
CAS No.:137792-58-6
Molecular Formula:C₂₆H₃₀O₅
Molecular Weight:422.521
Hs Code.:

Synonyms:

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Chemical Property of (E)-3-((2R,3S,4R)-3,4-Bis-benzyloxy-3,4-dihydro-2H-pyran-2-yl)-acrylic acid tert-butyl ester

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Technology Process of (E)-3-((2R,3S,4R)-3,4-Bis-benzyloxy-3,4-dihydro-2H-pyran-2-yl)-acrylic acid tert-butyl ester

There total 6 articles about (E)-3-((2R,3S,4R)-3,4-Bis-benzyloxy-3,4-dihydro-2H-pyran-2-yl)-acrylic acid tert-butyl ester 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:

: 87316-22-1
(2R,3S,4R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol

: 137792-58-6,137792-78-0
(E)-3-((2R,3S,4R)-3,4-Bis-benzyloxy-3,4-dihydro-2H-pyran-2-yl)-acrylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 65 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 9 h / Ambient temperature

2: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

3: pyridinium chlorochromate, 4-Angstroem molecular sieves / CH₂Cl₂

4: 1) NaH / 1) THF, 0 deg C, 15 min, 2) THF, -78 deg C

With 4 A molecular sieve; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00028a033

Reference yield:

: 100-39-0
benzyl bromide

: 137792-58-6,137792-78-0
(E)-3-((2R,3S,4R)-3,4-Bis-benzyloxy-3,4-dihydro-2H-pyran-2-yl)-acrylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 65 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 9 h / Ambient temperature

2: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

3: pyridinium chlorochromate, 4-Angstroem molecular sieves / CH₂Cl₂

4: 1) NaH / 1) THF, 0 deg C, 15 min, 2) THF, -78 deg C

With 4 A molecular sieve; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00028a033

Reference yield:

: 58871-10-6
3,4-di-O-benzyl-D-glucal

: 137792-58-6,137792-78-0
(E)-3-((2R,3S,4R)-3,4-Bis-benzyloxy-3,4-dihydro-2H-pyran-2-yl)-acrylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: pyridinium chlorochromate, 4-Angstroem molecular sieves / CH₂Cl₂

2: 1) NaH / 1) THF, 0 deg C, 15 min, 2) THF, -78 deg C

With 4 A molecular sieve; sodium hydride; pyridinium chlorochromate; In dichloromethane;
DOI:10.1021/jo00028a033