(E)-4-((2R,3S)-3-Hydroxy-tetrahydro-pyran-2-yl)-but-2-enoic acid benzyl ester

Base Information

Chemical Name:(E)-4-((2R,3S)-3-Hydroxy-tetrahydro-pyran-2-yl)-but-2-enoic acid benzyl ester
CAS No.:125878-04-8
Molecular Formula:C₁₆H₂₀O₄
Molecular Weight:276.332
Hs Code.:

Synonyms:(E)-4-((2R,3S)-3-Hydroxy-tetrahydro-pyran-2-yl)-but-2-enoic acid benzyl ester

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Chemical Property of (E)-4-((2R,3S)-3-Hydroxy-tetrahydro-pyran-2-yl)-but-2-enoic acid benzyl ester

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Technology Process of (E)-4-((2R,3S)-3-Hydroxy-tetrahydro-pyran-2-yl)-but-2-enoic acid benzyl ester

There total 11 articles about (E)-4-((2R,3S)-3-Hydroxy-tetrahydro-pyran-2-yl)-but-2-enoic acid benzyl 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:

: 125901-90-8
(2R,3S)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol

: 125878-04-8
(E)-4-((2R,3S)-3-Hydroxy-tetrahydro-pyran-2-yl)-but-2-enoic acid benzyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 95 percent / H₂ / 5percent Pd/C / methanol / 16 h / 25 °C

2: 92 percent / imidazole / dimethylformamide / 16 h / 25 °C

3: 72 percent / trifluoroacetic acid / tetrahydrofuran; H₂O / 0.17 h / 0 °C

4: oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

5: 82 percent / tetrahydrofuran / 1 h / 0 °C

6: 1.) 9-BBN, 2.) H₂O₂, 3 N NaOH / 1.) THF, 0 deg C, 3 h

7: 93 percent / 1.) (COCl)2, DMSO, 2.) Et₃N / CH₂Cl₂ / 1.) -78 deg C, 30 min

8: 98 percent / dimethylformamide / 0.5 h / 25 °C

9: 93 percent / n-Bu₄NF / tetrahydrofuran / 3 h / 25 °C

With 1H-imidazole; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ja00164a026

Reference yield:

: 149342-25-6,92131-91-4
((2R,3S)-3-acetoxy-3,6-dihydro-2H-pyran-2-yl)methyl acetate

: 125878-04-8
(E)-4-((2R,3S)-3-Hydroxy-tetrahydro-pyran-2-yl)-but-2-enoic acid benzyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 95 percent / NaOMe / methanol / 2 h / 25 °C

2: 95 percent / H₂ / 5percent Pd/C / methanol / 16 h / 25 °C

3: 92 percent / imidazole / dimethylformamide / 16 h / 25 °C

4: 72 percent / trifluoroacetic acid / tetrahydrofuran; H₂O / 0.17 h / 0 °C

5: oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

6: 82 percent / tetrahydrofuran / 1 h / 0 °C

7: 1.) 9-BBN, 2.) H₂O₂, 3 N NaOH / 1.) THF, 0 deg C, 3 h

8: 93 percent / 1.) (COCl)2, DMSO, 2.) Et₃N / CH₂Cl₂ / 1.) -78 deg C, 30 min

9: 98 percent / dimethylformamide / 0.5 h / 25 °C

10: 93 percent / n-Bu₄NF / tetrahydrofuran / 3 h / 25 °C

With 1H-imidazole; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium methylate; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ja00164a026

Reference yield:

: 2873-29-2
D-glucal triacetate

: 125878-04-8
(E)-4-((2R,3S)-3-Hydroxy-tetrahydro-pyran-2-yl)-but-2-enoic acid benzyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 94 percent / Et₃SiH, BF₃*Et₂O / CH₂Cl₂ / 0.5 h / 0 °C

2: 95 percent / NaOMe / methanol / 2 h / 25 °C

3: 95 percent / H₂ / 5percent Pd/C / methanol / 16 h / 25 °C

4: 92 percent / imidazole / dimethylformamide / 16 h / 25 °C

5: 72 percent / trifluoroacetic acid / tetrahydrofuran; H₂O / 0.17 h / 0 °C

6: oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

7: 82 percent / tetrahydrofuran / 1 h / 0 °C

8: 1.) 9-BBN, 2.) H₂O₂, 3 N NaOH / 1.) THF, 0 deg C, 3 h

9: 93 percent / 1.) (COCl)2, DMSO, 2.) Et₃N / CH₂Cl₂ / 1.) -78 deg C, 30 min

10: 98 percent / dimethylformamide / 0.5 h / 25 °C

11: 93 percent / n-Bu₄NF / tetrahydrofuran / 3 h / 25 °C

With 1H-imidazole; triethylsilane; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium methylate; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ja00164a026