Benzoic acid (3R,4S,5S,6R)-1-acetyl-4-hydroxy-5-(4-methoxy-benzyloxy)-6-(4-methoxy-phenoxymethyl)-piperidin-3-yl ester

Base Information

• Chemical Name: Benzoic acid (3R,4S,5S,6R)-1-acetyl-4-hydroxy-5-(4-methoxy-benzyloxy)-6-(4-methoxy-phenoxymethyl)-piperidin-3-yl ester
• CAS No.: 544455-48-3
• Molecular Formula: C₃₀H₃₃NO₈
• Molecular Weight: 535.594

Synonyms:Benzoic acid (3R,4S,5S,6R)-1-acetyl-4-hydroxy-5-(4-methoxy-benzyloxy)-6-(4-methoxy-phenoxymethyl)-piperidin-3-yl ester

Chemical Property of Benzoic acid (3R,4S,5S,6R)-1-acetyl-4-hydroxy-5-(4-methoxy-benzyloxy)-6-(4-methoxy-phenoxymethyl)-piperidin-3-yl ester

Chemical Property:

Purity/Quality:

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Technology Process of Benzoic acid (3R,4S,5S,6R)-1-acetyl-4-hydroxy-5-(4-methoxy-benzyloxy)-6-(4-methoxy-phenoxymethyl)-piperidin-3-yl ester

There total 14 articles about Benzoic acid (3R,4S,5S,6R)-1-acetyl-4-hydroxy-5-(4-methoxy-benzyloxy)-6-(4-methoxy-phenoxymethyl)-piperidin-3-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: 85.0%

sodium benzoate (532-32-1) + 1-[(3aS,6R,7S,7aR)-7-(4-Methoxy-benzyloxy)-6-(4-methoxy-phenoxymethyl)-2,2-dioxo-tetrahydro-1,3-dioxa-2λ6-thia-5-aza-inden-5-yl]-ethanone (544455-47-2) → Benzoic acid (3R,4S,5S,6R)-1-acetyl-4-hydroxy-5-(4-methoxy-benzyloxy)-6-(4-methoxy-phenoxymethyl)-piperidin-3-yl ester (544455-48-3)

Guidance literature:

sodium benzoate; 1-[(3aS,6R,7S,7aR)-7-(4-Methoxy-benzyloxy)-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 3h;

With sulfuric acid; In dichloromethane; at 25 ℃; for 12h;

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

Reference yield:

4-methoxy-phenol (150-76-5) → Benzoic acid (3R,4S,5S,6R)-1-acetyl-4-hydroxy-5-(4-methoxy-benzyloxy)-6-(4-methoxy-phenoxymethyl)-piperidin-3-yl ester (544455-48-3)

Guidance literature:

Multi-step reaction with 14 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: 96 percent / OsO₄; NMO / 2-methyl-propan-2-ol; H₂O / 12 h

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

12.1: NaIO₄ / RuCl₃ / acetonitrile; CH₂Cl₂; H₂O / 1 h / 25 °C

13.1: dimethylformamide / 3 h / 105 °C

13.2: 85 percent / aq. H₂SO₄ / CH₂Cl₂ / 12 h / 25 °C

With dmap; lithium hydroxide; potassium osmate(VI); sodium periodate; osmium(VIII) oxide; lithium borohydride; thionyl chloride; N-methyl-2-indolinone; 18-crown-ether; TEA; tetrabutyl ammonium fluoride; potassium hydride; sodium hydride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-bis(9-O-dihydroquinidine)phthalazine; lithium bromide; ruthenium trichloride; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 2.1: Sharpless asymmetric aminohydroxylation / 8.1: Dess-Martin oxidation / 9.1: Horner-Wadsworth-Emmons olefination / 10.1: ring closing metathesis / 11.1: Sharpless asymmetric dihydroxylation;

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

Reference yield:

ethyl (2E)-4-(4-methoxyphenoxy)but-2-enoate (544455-38-1) → Benzoic acid (3R,4S,5S,6R)-1-acetyl-4-hydroxy-5-(4-methoxy-benzyloxy)-6-(4-methoxy-phenoxymethyl)-piperidin-3-yl ester (544455-48-3)

Guidance literature:

Multi-step reaction with 13 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: 96 percent / OsO₄; NMO / 2-methyl-propan-2-ol; H₂O / 12 h

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

12.1: NaIO₄ / RuCl₃ / acetonitrile; CH₂Cl₂; H₂O / 1 h / 25 °C

13.1: dimethylformamide / 3 h / 105 °C

13.2: 85 percent / aq. H₂SO₄ / CH₂Cl₂ / 12 h / 25 °C

With dmap; lithium hydroxide; potassium osmate(VI); sodium periodate; osmium(VIII) oxide; lithium borohydride; thionyl chloride; N-methyl-2-indolinone; 18-crown-ether; TEA; tetrabutyl ammonium fluoride; potassium hydride; sodium hydride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-bis(9-O-dihydroquinidine)phthalazine; lithium bromide; ruthenium trichloride; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 1.1: Sharpless asymmetric aminohydroxylation / 7.1: Dess-Martin oxidation / 8.1: Horner-Wadsworth-Emmons olefination / 9.1: ring closing metathesis / 10.1: Sharpless asymmetric dihydroxylation;

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

upstream raw materials:

sodium benzoate

1-[(3aS,6R,7S,7aR)-7-(4-Methoxy-benzyloxy)-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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