Benzoic acid (2R,3R,4S,5R)-1-acetyl-3,5-dihydroxy-2-(4-methoxy-phenoxymethyl)-piperidin-4-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3R,4S,5R)-1-acetyl-3,5-dihydroxy-2-(4-methoxy-phenoxymethyl)-piperidin-4-yl ester
• CAS No.: 544455-58-5
• Molecular Formula: C₂₂H₂₅NO₇
• Molecular Weight: 415.443

Synonyms:Benzoic acid (2R,3R,4S,5R)-1-acetyl-3,5-dihydroxy-2-(4-methoxy-phenoxymethyl)-piperidin-4-yl ester

Chemical Property of Benzoic acid (2R,3R,4S,5R)-1-acetyl-3,5-dihydroxy-2-(4-methoxy-phenoxymethyl)-piperidin-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of Benzoic acid (2R,3R,4S,5R)-1-acetyl-3,5-dihydroxy-2-(4-methoxy-phenoxymethyl)-piperidin-4-yl ester

There total 17 articles about Benzoic acid (2R,3R,4S,5R)-1-acetyl-3,5-dihydroxy-2-(4-methoxy-phenoxymethyl)-piperidin-4-yl 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: 80.0%

sodium benzoate (532-32-1) + 1-[(3aR,6R,7R,7aS)-7-(tert-Butyl-diphenyl-silanyloxy)-6-(4-methoxy-phenoxymethyl)-2,2-dioxo-tetrahydro-1,3-dioxa-2λ6-thia-5-aza-inden-5-yl]-ethanone (544455-56-3) → Benzoic acid (2R,3R,4S,5R)-1-acetyl-3,5-dihydroxy-2-(4-methoxy-phenoxymethyl)-piperidin-4-yl ester (544455-58-5) + Benzoic acid (2R,3R,4S,5R)-1-acetyl-3-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-2-(4-methoxy-phenoxymethyl)-piperidin-4-yl ester (544455-57-4)

Guidance literature:

sodium benzoate; 1-[(3aR,6R,7R,7aS)-7-(tert-Butyl-diphenyl-silanyloxy)-6-(4-methoxy-phenoxymethyl)-2,2-dioxo-tetrahydro-1,3-dioxa-2λ⁶-thia-5-aza-inden-5-yl]-ethanone; In N,N-dimethyl-formamide; at 105 ℃; for 5h;

With sulfuric acid; In dichloromethane; at 25 ℃; for 12h; Title compound not separated from byproducts;

DOI:10.1016/S0040-4039(03)00218-1

Reference yield:

4-methoxy-phenol (150-76-5) → Benzoic acid (2R,3R,4S,5R)-1-acetyl-3,5-dihydroxy-2-(4-methoxy-phenoxymethyl)-piperidin-4-yl ester (544455-58-5)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 70 percent / K₂OsO₄*2H₂O; (DHQD)2PHAL; LiOH / 2-methyl-propan-2-ol; H₂O / 8 h / 4 °C

2.1: 80 percent / NaH / dimethylformamide / 8 h / 0 °C

3.1: 100 percent / LiBH₄ / diethyl ether / 0.25 h

4.1: 100 percent / TEA; DMAP / CH₂Cl₂ / 4 h / 25 °C

5.1: 95 percent / KH; 18-crown-ether / tetrahydrofuran / 5 h / 25 °C

6.1: 100 percent / tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 25 °C

7.1: 90 percent / periodinane / CH₂Cl₂ / 1 h / 25 °C

8.1: 94 percent / LiBr; DBU / tetrahydrofuran / 2 h / 25 °C

9.1: 80 percent / Grubb's bis(tricyclohexylphosphinebenzylidene Ru(IV)Cl₂ / toluene / 2 h / 90 °C

10.1: 85 percent / trifluoroacetic acid / CH₂Cl₂ / 0.5 h / 25 °C

11.1: 80 percent / DIPAD; Ph₃P / tetrahydrofuran / 2 h / 0 °C

12.1: 100 percent / K₂CO₃ / methanol / 5 h / 25 °C

13.1: 93 percent / imidazole; TEA / dimethylformamide / 12 h / 60 °C

14.1: 94 percent / K₂OsO₄*2H₂O; NMO / 2-methyl-propan-2-ol; H₂O / 16 h

15.1: thionyl chloride; TEA / CH₂Cl₂ / 0.5 h / -15 °C

15.2: 66 percent / NaIO₄ / RuCl₃ / acetonitrile; CH₂Cl₂; H₂O / 1 h / 25 °C

16.1: dimethylformamide / 5 h / 105 °C

16.2: aq. H₂SO₄ / CH₂Cl₂ / 12 h / 25 °C

With 1H-imidazole; dmap; lithium hydroxide; potassium osmate(VI); lithium borohydride; thionyl chloride; N-methyl-2-indolinone; 18-crown-ether; TEA; tetrabutyl ammonium fluoride; potassium hydride; sodium hydride; potassium carbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropyl (E)-azodicarboxylate; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; trifluoroacetic acid; lithium bromide; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 2.1: Sharpless asymmetric aminohydroxylation / 8.1: Dess-Martin oxidation / 9.1: Horner-Wadsworth-Emmons olefination / 10.1: ring closing metathesis / 12.1: Mitsunobu reaction / 15.1: Sharpless-Upjohn dihydroxylation;

DOI:10.1016/S0040-4039(03)00218-1

Reference yield:

ethyl (2E)-4-(4-methoxyphenoxy)but-2-enoate (544455-38-1) → Benzoic acid (2R,3R,4S,5R)-1-acetyl-3,5-dihydroxy-2-(4-methoxy-phenoxymethyl)-piperidin-4-yl ester (544455-58-5)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 70 percent / K₂OsO₄*2H₂O; (DHQD)2PHAL; LiOH / 2-methyl-propan-2-ol; H₂O / 8 h / 4 °C

2.1: 80 percent / NaH / dimethylformamide / 8 h / 0 °C

3.1: 100 percent / LiBH₄ / diethyl ether / 0.25 h

4.1: 100 percent / TEA; DMAP / CH₂Cl₂ / 4 h / 25 °C

5.1: 95 percent / KH; 18-crown-ether / tetrahydrofuran / 5 h / 25 °C

6.1: 100 percent / tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 25 °C

7.1: 90 percent / periodinane / CH₂Cl₂ / 1 h / 25 °C

8.1: 94 percent / LiBr; DBU / tetrahydrofuran / 2 h / 25 °C

9.1: 80 percent / Grubb's bis(tricyclohexylphosphinebenzylidene Ru(IV)Cl₂ / toluene / 2 h / 90 °C

10.1: 85 percent / trifluoroacetic acid / CH₂Cl₂ / 0.5 h / 25 °C

11.1: 80 percent / DIPAD; Ph₃P / tetrahydrofuran / 2 h / 0 °C

12.1: 100 percent / K₂CO₃ / methanol / 5 h / 25 °C

13.1: 93 percent / imidazole; TEA / dimethylformamide / 12 h / 60 °C

14.1: 94 percent / K₂OsO₄*2H₂O; NMO / 2-methyl-propan-2-ol; H₂O / 16 h

15.1: thionyl chloride; TEA / CH₂Cl₂ / 0.5 h / -15 °C

15.2: 66 percent / NaIO₄ / RuCl₃ / acetonitrile; CH₂Cl₂; H₂O / 1 h / 25 °C

16.1: dimethylformamide / 5 h / 105 °C

16.2: aq. H₂SO₄ / CH₂Cl₂ / 12 h / 25 °C

With 1H-imidazole; dmap; lithium hydroxide; potassium osmate(VI); lithium borohydride; thionyl chloride; N-methyl-2-indolinone; 18-crown-ether; TEA; tetrabutyl ammonium fluoride; potassium hydride; sodium hydride; potassium carbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropyl (E)-azodicarboxylate; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; trifluoroacetic acid; lithium bromide; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1.1: Sharpless asymmetric aminohydroxylation / 7.1: Dess-Martin oxidation / 8.1: Horner-Wadsworth-Emmons olefination / 9.1: ring closing metathesis / 11.1: Mitsunobu reaction / 14.1: Sharpless-Upjohn dihydroxylation;

DOI:10.1016/S0040-4039(03)00218-1

upstream raw materials:

sodium benzoate

1-[(3aR,6R,7R,7aS)-7-(tert-Butyl-diphenyl-silanyloxy)-6-(4-methoxy-phenoxymethyl)-2,2-dioxo-tetrahydro-1,3-dioxa-2λ⁶-thia-5-aza-inden-5-yl]-ethanone

4-methoxy-phenol

ethyl (2E)-4-(4-methoxyphenoxy)but-2-enoate

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