Benzoic acid (1R,2S,4R)-2-hydroxymethyl-4-(tetrahydro-pyran-2-yloxy)-cyclopentyl ester

Base Information

Chemical Name:Benzoic acid (1R,2S,4R)-2-hydroxymethyl-4-(tetrahydro-pyran-2-yloxy)-cyclopentyl ester
CAS No.:341554-02-7
Molecular Formula:C₁₈H₂₄O₅
Molecular Weight:320.386
Hs Code.:

Synonyms:Benzoic acid (1R,2S,4R)-2-hydroxymethyl-4-(tetrahydro-pyran-2-yloxy)-cyclopentyl ester

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Chemical Property of Benzoic acid (1R,2S,4R)-2-hydroxymethyl-4-(tetrahydro-pyran-2-yloxy)-cyclopentyl ester

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Technology Process of Benzoic acid (1R,2S,4R)-2-hydroxymethyl-4-(tetrahydro-pyran-2-yloxy)-cyclopentyl ester

There total 11 articles about Benzoic acid (1R,2S,4R)-2-hydroxymethyl-4-(tetrahydro-pyran-2-yloxy)-cyclopentyl 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: 100.0%

: 341554-01-6
Benzoic acid (1R,2S,4R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-(tetrahydro-pyran-2-yloxy)-cyclopentyl ester

: 341554-02-7
Benzoic acid (1R,2S,4R)-2-hydroxymethyl-4-(tetrahydro-pyran-2-yloxy)-cyclopentyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;
DOI:10.1021/ol015783n

Reference yield:

: 192118-38-0
(1R,2R,3S,4S)-4-(tert-butoxymethyl)-2,3-(isopropylidenedioxy)cyclopentan-1-ol

: 341554-02-7
Benzoic acid (1R,2S,4R)-2-hydroxymethyl-4-(tetrahydro-pyran-2-yloxy)-cyclopentyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: 88 percent / NaH / tetrahydrofuran / 0 °C

2.1: 97 percent / TFA / H₂O / 60 °C

3.1: 79 percent / pyridine / 0 °C

4.1: NaH; CS₂; MeI / tetrahydrofuran / 0 - 20 °C

4.2: 76 percent / Bu₃SnH; AIBN / toluene / Heating

5.1: 82 percent / H₂ / Pd(OH)2 / methanol

6.1: 85 percent / PPTS / CH₂Cl₂ / 20 °C

7.1: 84 percent / TBAF / tetrahydrofuran / 20 °C

8.1: 99 percent / imidazole / tetrahydrofuran / 0 - 20 °C

9.1: 98 percent / pyridine / 0 °C

10.1: 100 percent / TBAF / tetrahydrofuran / 20 °C

With 1H-imidazole; carbon disulfide; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; trifluoroacetic acid; methyl iodide; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; water;
DOI:10.1021/ol015783n

Reference yield:

: 341553-94-4
(-)-(1R,2S,3S,4R)-1-O-benzyloxy-2,3-dihydroxyl-4-hydroxymethylcyclopentane

: 341554-02-7
Benzoic acid (1R,2S,4R)-2-hydroxymethyl-4-(tetrahydro-pyran-2-yloxy)-cyclopentyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 79 percent / pyridine / 0 °C

2.1: NaH; CS₂; MeI / tetrahydrofuran / 0 - 20 °C

2.2: 76 percent / Bu₃SnH; AIBN / toluene / Heating

3.1: 82 percent / H₂ / Pd(OH)2 / methanol

4.1: 85 percent / PPTS / CH₂Cl₂ / 20 °C

5.1: 84 percent / TBAF / tetrahydrofuran / 20 °C

6.1: 99 percent / imidazole / tetrahydrofuran / 0 - 20 °C

7.1: 98 percent / pyridine / 0 °C

8.1: 100 percent / TBAF / tetrahydrofuran / 20 °C

With 1H-imidazole; carbon disulfide; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; methyl iodide; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; dichloromethane;
DOI:10.1021/ol015783n