(-)-(1S,4R)-camphanic acid [((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]ester

Base Information

• Chemical Name: (-)-(1S,4R)-camphanic acid [((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]ester
• CAS No.: 432036-82-3
• Molecular Formula: C₂₈H₃₂O₆
• Molecular Weight: 464.558
• Mol file: 432036-82-3.mol

Synonyms:(-)-(1S,4R)-camphanic acid [((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]ester

Chemical Property of (-)-(1S,4R)-camphanic acid [((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1S,4R)-camphanic acid [((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]ester

There total 12 articles about (-)-(1S,4R)-camphanic acid [((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]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: 34.0%

(-)-(1S,4R)-camphanic acid [(5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]ester (432036-81-2) → (-)-(1S,4R)-camphanic acid [((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]ester (432036-82-3) + (-)-(1S,4R)-camphanic acid [((2S)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]ester (432036-84-5)

Guidance literature:

In ethanol; at 20 - 80 ℃; Solvent; Resolution of racemate; Large scale;

DOI:10.1021/op3003085

Reference yield:

4-benzyloxy-1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirane (314289-66-2) → (-)-(1S,4R)-camphanic acid [((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]ester (432036-82-3) + (-)-(1S,4R)-camphanic acid [((2S)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]ester (432036-84-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: toluene-4-sulfonic acid / toluene / 1 h / 85 - 90 °C / Large scale

2.1: trimethylsulfoxonium iodide; potassium tert-butylate / toluene / 2 h / 20 - 80 °C / Large scale

2.2: Large scale

3.1: toluene-4-sulfonic acid / tetrahydrofuran; water / 3 h / 20 - 35 °C / Large scale

4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / N,N-dimethyl-formamide / 2 h / 5 - 10 °C / Large scale

5.1: ethanol / 20 - 80 °C / Resolution of racemate; Large scale

With dmap; potassium tert-butylate; trimethylsulfoxonium iodide; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; toluene; 1.1: |Meinwald Rearrangement;

DOI:10.1021/op3003085

Reference yield:

5-benzyloxy-1,2,3,4-tetrahydro-naphthalen-1-one (90401-60-8) → (-)-(1S,4R)-camphanic acid [((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]ester (432036-82-3) + (-)-(1S,4R)-camphanic acid [((2S)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]ester (432036-84-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium tetrahydroborate / toluene; ethanol / 1 h / 5 - 30 °C / Large scale

2.1: potassium hydrogensulfate / toluene / 1 h / Reflux; Large scale

3.1: 3-chloro-benzenecarboperoxoic acid / toluene / 1.5 h / 5 - 30 °C / Large scale

4.1: toluene-4-sulfonic acid / toluene / 1 h / 85 - 90 °C / Large scale

5.1: trimethylsulfoxonium iodide; potassium tert-butylate / toluene / 2 h / 20 - 80 °C / Large scale

5.2: Large scale

6.1: toluene-4-sulfonic acid / tetrahydrofuran; water / 3 h / 20 - 35 °C / Large scale

7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / N,N-dimethyl-formamide / 2 h / 5 - 10 °C / Large scale

8.1: ethanol / 20 - 80 °C / Resolution of racemate; Large scale

With dmap; sodium tetrahydroborate; potassium hydrogensulfate; potassium tert-butylate; trimethylsulfoxonium iodide; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; toluene; 4.1: |Meinwald Rearrangement;

DOI:10.1021/op3003085

upstream raw materials:

4-benzyloxy-1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirane

5-benzyloxy-1,2,3,4-tetrahydro-2-oxonaphthalene

5-benzyloxy-1,23,4-tetrahydrospiro[naphthalene-2,2'-oxirane]

(5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methanol

Downstream raw materials:

((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methanol

(-)-camphanic acid

diphenylcarbamic acid [((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]ester

diphenylcarbamic acid ((2R)-2,5-dihydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl ester

Refernces